Electrophotographic photoconductor containing disazo and trisazo pigments

ABSTRACT

An electrophotographic photoconductor includes an electroconductive support and a single-layered photoconductive layer formed thereon, containing a charge transporting material, a binder resin, and a simultaneously pulverized mixture including at least one disazo pigment of formula (1) and at least one trisazo pigment of formula (2), which is obtained by simultaneously pulverizing those azo pigments: ##STR1## wherein R 1  and R 2  each is hydrogen, a halogen atom, trifluoromethyl group, nitro group or cyano group; R 3  is hydrogen, chlorine, fluorine, iodine, bromine, nitro group or cyano group; and Ar 1 , Ar 2  and Ar 3  each is a coupler radical, which may be the same or different.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to an electrophotographic photoconductor and, more particularly to a single-layered organic electrophotographic photoconductor for use in electrophotographic copying machines and printers.

2. Discussion of Background

Inorganic photoconductive materials such as selenium, zinc oxide and cadmium sulfide; organic photoconductive materials such as azo pigments; and amorphous silicon, are conventionally known as photoconductive materials for use in electrophotographic photoconductors. However, the inorganic photoconductive materials have the drawbacks in photosensitivity, thermal stability, durability, impact resistance, and toxicity. For instance, selenium easily tends to crystallize, for example, when inappropriately heated, so that the characteristics readily deteriorate. A photoconductor employing cadmium sulfide or zinc oxide as a photoconductive material has humidity resistance and durability. The organic photoconductive materials can easily be made into a film with much more design freedom than the inorganic photoconductive materials because of the superior film-forming properties of the organic photoconductive materials.

In addition, the organic photoconductive materials are cheaper and cause no environmental pollution problems, so that electrophotographic photoconductors using the organic photoconductive materials have been actively developed in recent years.

Photoconductors comprising such organic photoconductive materials may be classified into two types, that is, a function-separated type photoconductor comprising a charge generation layer and a charge transport layer which are laminated, and a single-layered photoconductor comprising a photoconductive layer in which a charge generating material is dispersed in a binder resin.

In particular, many function-separated type photoconductors are put to practical use because of their superiority in photosensitivity.

For example, a function-separated laminated photoconductor comprising Chloro Diane Blue and a hydrazone compound in combination is proposed in Japanese Patent Publication 55-42380. Charge generating materials for use in such a function-separated laminated photoconductor are disclosed in Japanese Laid-Open Patent Applications 53-133445, 54-21728 and 54-22834; and charge transporting materials are disclosed in Japanese Laid-Open Patent Applications 58-198043 and 58-199352.

When preparing a laminated photoconductor, however, it is necessary to severely control the thickness of a charge generation layer within a range of 0.1 to 1.0 μm for obtaining high photosensitivity. Such thickness control of the charge generation layer is susceptible to the surface conditions of an electroconductive support on which the charge generation layer is provided, and to the ambient conditions while a charge generation coating liquid is applied onto the support. Furthermore, for the preparation of such a laminated photoconductor comprising the charge generation layer and the charge transport layer, at least two coating steps are required. These factors largely affect the yield and manufacturing cost of the photoconductor.

For obtaining a laminated photoconductor with high photosensitivity, a charge transporting material with high electric charge mobility is demanded for use in the charge transport layer. Charge transporting materials with high electric charge mobility are almost limited to compounds which exhibit positive hole transporting characteristics. Therefore, photoconductors for use in practice are necessarily limited to photoconductors of a negative charging type, which are referred to as negatively-chargeable photoconductors.

Most of negatively-chargeable photoconductors are charged by use of corona charge with a negative polarity, so that a large amount of ozone is generated. The thus generated ozone is harmful to the human body, and impairs the photoconductor itself by the reaction with ozone, thereby shortening the life thereof. To prevent the generation of ozone, there are proposed a charging system capable of hindering the generation of ozone, a special system for decomposing the ozone discharged from a charging unit, and a special ozone exhaust system for removing ozone built up in an electrophotographic copying machine. Although some of these systems have been put to practical use, such systems have the shortcomings that they will make electrophotographic process complicated.

On the other hand, the single-layered electrophotographic photoconductors are generally known as positively-chargeable photoconductors. For example, there are proposed a photoconductor comprising polyvinyl carbazole and 2,4,7-trinitro-9-fluorenone in Japanese Patent Publication 50-10496; a photoconductor comprising a polyvinyl carbazole which is sensitized with a pyrylium salt-based pigment in Japanese Patent Publication 48-25658; a photoconductor comprising as a main component a eutectic complex; a photoconductor comprising a charge generating material and a charge transporting material in Japanese Laid-Open Patent Application 47-30330; photoconductors comprising a perylene pigment and a charge transporting material in Japanese Laid-Open Patent Applications 63-271461, 1-118143 and 3-65961; and a photoconductor comprising a phthalocyanine compound and a binder resin in Japanese Laid-Open Patent Application 3-65961.

However, the above-mentioned conventional single-layered photoconductors are still inferior in photosensitivity to the laminated photoconductors and the photosensitivity thereof is insufficient for use in practice.

In line with the recent trend of function-composition and improvement of copying machine, photoconductors capable of coping with a copying machine provided with both analog and digital functions have been developed. More specifically, to cope with the digital function of copying machine, it is desired that the photoconductor be highly photosensitive in a region with a wavelength of light from LD laser power source, namely, in the near infrared region; and to cope with the analog function of copying machine, it is required that the photoconductor be highly photosensitive in a region with the wavelength of white light, namely, in the visible region.

Function-separated laminated photoconductors which have a broad spectral sensitivity ranging from the visible region through the near infrared region are disclosed in Japanese Laid-Open Patent Applications 63-236047, 63-243950, 63-243951 and 1-315752, each of which comprises a mixture of a pigment having photosensitivity in the visible region and a pigment having photosensitivity in the near infrared region.

However, the charge transport layer is generally provided on the charge generation layer comprising the above-mentioned pigments and the charge transporting material contained in the charge transport layer absorbs light, so that the photosensitivity to light with a short wavelength of the function-separated laminated photoconductor is low. Thus, the spectral sensitivities of the conventional laminated photoconductors from the visible region to the near infrared region are not always sufficient for use in practice.

In addition, the laminated photoconductor has the optical problem of generation of interference light because of the presence of an interface between the charge generation layer and the charge transport layer.

SUMMARY OF THE INVENTION

It is therefore an object of the present invention to provide a single-layered electrophotographic photoconductor having high photosensitivities in a broad wave range including a visible region through a near infrared region, and having excellent performance stability and improved charging characteristics even when used repeatedly in electrophotographic image formation, which can be manufactured at a low cost.

The above object of the present invention can be attained by an electrophotographic photoconductor comprising an electroconductive support and a single-layered photoconductive layer formed thereon, comprising a charge transporting material, a binder resin, and a simultaneously pulverized mixture comprising at least one disazo pigment of formula (1) and at least one trisazo pigment of formula (2), which is obtained by simultaneously pulverizing the disazo pigment and the trisazo pigment: ##STR2## wherein R¹ and R² each is hydrogen, a halogen atom, trifluoromethyl group, nitro group or cyano group; R³ is hydrogen, chlorine, fluorine, iodine, bromine, nitro group or cyano group; and Ar¹, Ar² and Ar³ each is a coupler radical, which may be the same or different, and is selected from the group consisting of coupler radicals of formulas (3) to (10): ##STR3## wherein X¹ is --OH, --N(R⁴)(R⁵), or --NHSO₂ R⁶, in which R⁴ and R⁵ each is hydrogen, an acyl group or an alkyl group which may have a substituent, and R⁶ is an aryl group which may have a substituent; Y¹ is hydrogen, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group, a carboxyl group, a sulfone group, a benzimidazolyl group, a sulfamoyl group which may have a substituent, or --CON(R⁷)(Y²), in which R⁷ is hydrogen, an alkyl group which may have a substituent, or a phenyl group which may have a substituent, and Y² is a cyclic hydrocarbon group which may have a substituent, a heterocyclic group which may have a substituent, or --N═C(R⁸)(R⁹), in which R⁸ is a cyclic hydrocarbon group which may have a substituent, a heterocyclic group which may have a substituent, or a styryl group which may have a substituent, R⁹ is hydrogen, an alkyl group which may have a substituent, or a phenyl group which may have a substituent, and R⁸ and R⁹ may form a ring in combination with a carbon atom to which R⁸ and R⁹ are bonded; and Z is a cyclic hydrocarbon group which may have a substituent, or a heterocyclic group which may have a substituent; ##STR4## wherein n is an integer of 1 to 4; R¹⁰ is hydrogen, an alkyl group which may have a substituent, or an aryl group which may have a substituent; R¹¹ is hydrogen, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an alkylsulfonyl group which may have a substituent, an alkylmercapto group which may have a substituent, a halogen atom, an aryl group which may have a substituent, an acyl group which may have a substituent, cyano group, nitro group, or an amino group which may have a substituent, and when n is 2, 3 or 4, R¹¹ may be the same or different; and Y¹ is the same as defined in formula (3); ##STR5## wherein R¹² in formulas (5) and (6) is a hydrocarbon group which may have a substituent; ##STR6## wherein R¹³ in formulas (7) and (8) is an alkyl group, a carbamoyl group, a carboxyl group or an ester group thereof; and Ar⁴ is an aromatic hydrocarbon group which may have a substituent; ##STR7## wherein X² in formulas (9) and (10) is a bivalent aromatic hydrocarbon group or a bivalent heterocyclic group.

In the first mentioned electrophotographic photoconductor, the charge transporting material may be an organic positive hole transporting material, or may comprise an organic positive hole transporting material and an organic acceptor compound.

When the electrophotographic photoconductor comprise an organic positive hole transporting material and an organic acceptor compound, the organic acceptor compound may have a reduction potential in a range of -0.2 to -1.2 v (vs SCE).

In the first mentioned electrophotographic photoconductor, the single-layered photoconductive layer may further comprise an antioxidant.

BRIEF DESCRIPTION OF THE DRAWINGS

A more complete appreciation of the invention and many of the attendant advantages thereof will be readily obtained as the same becomes better understood by reference to the following detailed description when considered in connection with the accompanying drawings, wherein:

FIG. 1 is a schematic cross-sectional view of a first embodiment of an electrophotographic photoconductor according to the present invention, which comprises an electroconductive layer and a photoconductive layer formed on the electroconductive layer;

FIG. 2 is a schematic cross-sectional view of a second embodiment of an electrophotographic photoconductor according to the present invention, in which an undercoat layer is provided between an electroconductive support and an photoconductive layer;

FIG. 3 is a schematic cross-sectional view of a third embodiment of an electrophotographic photoconductor according to the present invention, in which a protective layer is provided on a photoconductive layer;

FIG. 4 is a schematic cross-sectional view of a fourth embodiment of an electrophotographic photoconductor according to the present invention, in which an undercoat layer is provided between an electroconductive support and a photoconductive layer, and a protective layer is provided on the photoconductive layer;

FIG. 5 is a graph which shows the relationship between the oxidation potential of a charge transporting material to be employed and the charging potential of the obtained photoconductor; and

FIG. 6 is a graph which shows the spectral sensitivities of a comparative photoconductor and a photoconductor according to the present invention.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

In the electrophotographic photoconductor according to the present invention, a disazo pigment having the sensitivity to the visible region, and a trisazo pigment having the sensitivity to the light with a wavelength of 700 nm or more, namely, to the near infrared rays, are simultaneously mixed and pulverized, and the thus simultaneously pulverized mixture is contained in a single-layered photoconductive layer.

The thus formed photoconductor exhibits high photosensitivities in a broad region, from the visible region to the near infrared region.

The photosensitivities of the disazo pigment and the trisazo pigment can be remarkably increased by simultaneously pulverizing and mixing these pigments together with the application of some mechanical energy thereto, as compared with the case where the abovementioned two kinds of pigments are merely contained in the photoconductive layer. Such a sensitizing effect can be proved by examples to be described later.

The mixing ratio of the disazo pigment to the trisazo pigment for use in the present invention can be determined depending upon the kinds of disazo pigment and trisazo pigment employed, and upon the characteristics required for the obtained photoconductor, such as photosensitivity, charging characteristics, and resistance to gases.

Generally, however, it is preferable that the mixing ratio of the disazo pigment to the trisazo pigment in terms of (Disazo Pigment)/(Disazo Pigment+Trisazo Pigment) be in a range of 0.01 to 0.99, namely 0.01≦(Disazo Pigment)/(Disazo Pigment+Trisazo Pigment)≦0.99.

A sufficiently high sensitizing effect can be obtained effectively when the above ratio is 0.01 or more, while the sensitizing effect and the resistance to gases can be improved when the ratio is 0.99 or less.

When uniform spectral photosensitivity in the visible region range through the near infrared region is taken into consideration, it is desirable that the above ratio be in the range of 0.1 to 0.9, namely, 0.1≦(Disazo Pigment)/(Disazo Pigment+Trisazo Pigment)≦0.9.

To mix and pulverize the disazo pigment and the trisazo pigment, any pulverizing and mixing methods can be employed as long as mechanical energy, such as compression, shearing, grinding, friction, stretching, shock and vibration may be applied to the pigments. For example, a ball mill, a vibration mill, a disk-vibration mill, an attritor, a sand mill, a paint shaker, a jet mil, and an ultrasonic dispersion mixer are usable. It is recommendable that desired amounts of the disazo pigment and the trisazo pigment be placed in the same container, and simultaneously pulverized and dispersed with the application of the above-mentioned mechanical energy thereto in the presence of a dispersing solvent.

A mixture of the disazo pigment and the trisazo pigment is used as a charge generating material in the electrophotographic photoconductor of the present invention. In particular, a disazo pigment of formula (1), which can efficiently generate electric charges when exposed to light in the visible range of 400 to 700 nm, and a trisazo pigment of formula (2), which has high sensitivity to light with a wavelength of 700 nm or more are employed in the present invention: ##STR8## wherein Ar¹, Ar² and Ar³ each is a coupler radical, which may be the same or different; R¹ and R² each is hydrogen, a halogen, trifluoromethyl group, nitro group or cyano group; and R³ is hydrogen, chlorine, fluorine, iodine, bromine, nitro group or cyano group.

The coupler radical represented by Ar¹, Ar² or Ar³ is selected from the group consisting of coupler radicals of formulas (3) to (10): ##STR9## wherein X¹ is --OH, --N(R⁴)(R⁵), or --NHSO₂ R⁶, in which R⁴ and R⁵ each is hydrogen, an acyl group or an alkyl group which may have a substituent, and R⁶ is an aryl group which may have a substituent; Y¹ is hydrogen, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group, a carboxyl group, a sulfone group, a benzimidazolyl group, a sulfamoyl group which may have a substituent, or --CON(R⁷)(Y²), in which R⁷ is hydrogen, an alkyl group which may have a substituent, or a phenyl group which may have a substituent, and Y² is a cyclic hydrocarbon group which may have a substituent, a heterocyclic group which may have a substituent, or --N═C(R⁸)(R⁹), in which R⁸ is a cyclic hydrocarbon group which may have a substituent, a heterocyclic group which may have a substituent, or a styryl group which may have a substituent, R⁹ is hydrogen, an alkyl group which may have a substituent, or a phenyl group which may have a substituent, and R⁸ and R⁹ may form a ring in combination with a carbon atom to which R⁸ and R⁹ are bonded; and Z is a cyclic hydrocarbon group which may have a substituent, or a heterocyclic group which may have a substituent; ##STR10## wherein n is an integer of 1 to 4; R¹⁰ is hydrogen, an alkyl group which may have a substituent, or an aryl group which may have a substituent; R¹¹ is hydrogen, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an alkylsulfonyl group which may have a substituent, an alkylmercapto group which may have a substituent, a halogen atom, an aryl group which may have a substituent, an acyl group which may have a substituent, cyano group, nitro group, or an amino group which may have a substituent, and when n is 2, 3 or 4, R¹¹ may be the same or different; and Y¹ is the same as defined in formula (3); ##STR11## wherein R¹² in formulas (5) and (6) is a hydrocarbon

group which may have a substituent; ##STR12## wherein R¹³ in formulas (7) and (8) is an alkyl group, a carbamoyl group, a carboxyl group or an ester group thereof; and Ar⁴ is an aromatic hydrocarbon group which may have a substituent; ##STR13## wherein X² in formulas (9) and (10) is a bivalent aromatic hydrocarbon group or a bivalent heterocyclic group.

Specific examples of the coupler which can be represented by Ar¹ --H, Ar² --H or Ar³ --H for preparation of the disazo pigment of formula (1) and the trisazo pigment of formula (2) are as shown in Table 1 to Table 16.

                  TABLE 1                                                          ______________________________________                                          ##STR14##                                                                     Coupler                          Melting Point                                 No.    R.sup.1     (R.sup.2).sub.n                                                                              (°C.)                                  ______________________________________                                          1     H           H             243-244                                        2     H           2-NO.sub.2    194-196                                        3     H           3-NO.sub.2    246-247                                        4     H           4-NO.sub.2      266-267.5                                    5     H           2-CF.sub.3    178-179                                        6     H           3-CF.sub.3    237.5-238.5                                    7     H           4-CF.sub.3    279-281                                        8     H           2-CN            221-222.5                                    9     H           3-CN          256.5-258.5                                   10     H           4-CN          274.5-277                                     11     H           2-l             199-199.5                                   12     H           3-l           258.5-259.5                                   13     H           4-l           261.5-262                                     14     H           2-Br          217-218                                       15     H           3-Br          254-255                                       16     H           4-Br          265-268                                       17     H           2-Cl          228-230                                       18     H           3-Cl          256.5-257                                     19     H           4-Cl          264-266                                       20     H           2-F           223.0-224.0                                   21     H           3-F           250.0-251.0                                   22     H           4-F           265.0-267.0                                   23     H           2-CH.sub.3    195.5-198.0                                   24     H           3-CH.sub.3    214.5-216.5                                   25     H           4-CH.sub.3    227.0-229.0                                   26     H           2-C.sub.2 H.sub.5                                                                            168.5-169.5                                   27     H           4-C.sub.2 H.sub.5                                                                            203.0-204.5                                   28     H           2-OCH.sub.3   167-168                                       29     H           3-OCH.sub.3   195.5-198.0                                   30     H           4-OCH.sub.3   229-230                                       31     H           2-OC.sub.2 H.sub.5                                                                           157-158                                       32     H           3-OC.sub.2 H.sub.5                                                                           188.5-189.0                                   33     H           4-OC.sub.2 H.sub.5                                                                           225.0-225.5                                   34     H           4-N(CH.sub.3).sub.2                                                                          232.0-233.5                                   35     CH.sub.3    H             189.5-190.5                                   36                                                                                     ##STR15##  H             182.0-183.0                                   37     H           2-OCH.sub.3, 5-OCH.sub.3                                                                     186.0-188.0                                   38     H           2-OC.sub.2 H.sub.5, 5-OC.sub.2 H.sub.5                                                       173.0-173.5                                   39     H           2-CH.sub.3, 5-CH.sub.3                                                                       207.0-208.5                                   40     H           2-Cl, 5-Cl    253.5-254.5                                   41     H           2-CH.sub.3, 5-Cl                                                                             245-247                                       42     H           2-OCH.sub.3, 4-OCH.sub.3                                                                     151.0-152.0                                   43     H           2-CH.sub.3, 4-CH.sub.3                                                                       226-228                                       44     H           2-CH.sub.3, 4-Cl                                                                             244-245                                       45     H           2-NO.sub.2, 4-OCH.sub.3                                                                      179.5-181.0                                   46     H           3-OCH.sub.3, 5-OCH.sub.3                                                                     180.5-182.0                                   47     H           2-OCH.sub.3, 5-Cl                                                                            219.0-220.0                                   48     H           2-OCH.sub.3, 5-OCH.sub.3,                                                                    193.5-195.5                                                      4-Cl                                                        49     H           2-OCH.sub.3, 4-OCH.sub.3,                                                                    193-194                                                          5-Cl                                                        50     H           3-Cl, 4-Cl    272.5-273.5                                   51     H           2-Cl, 4-Cl, 5-Cl                                                                             257.5-258.5                                   52     H           2-CH.sub.3, 3-Cl                                                                             227.5-228.5                                   53     H           3-Cl, 4-CH.sub.3                                                                             259.5-260.5                                   54     H           2-F, 4-F      246.0-246.5                                   55     H           2-F, 5-F      259.0-260.0                                   56     H           2-Cl, 4-NO.sub.2                                                                             283.0-284.0                                   57     H           2-NO.sub.2, 4-Cl                                                                             216.5-227.5                                   58     H           2-Cl, 3-Cl,   280.0-281.5                                                      4-Cl, 5-Cl                                                  59     H           4-OH          268                                           ______________________________________                                    

                  TABLE 2                                                          ______________________________________                                          ##STR16##                                                                     Coupler                        Melting Point                                   No.      R.sup.1 (R.sup.2).sub.n                                                                              (°C.)                                    ______________________________________                                         60       H       H             >300                                            61       H       2-NO.sub.2    283-284                                         62       H       3-NO.sub.2    >300                                            63       H       4-NO.sub.2    >300                                            64       H       2-Cl          >300                                            65       H       3-Cl          >300                                            66       H       4-Cl          >300                                            67       H       2-CH.sub.3    >300                                            68       H       3-CH.sub.3    >300                                            69       H       4-CH.sub.3    >300                                            70       H       2-C.sub.2 H.sub.5                                                                            271-273                                         71       H       4-C.sub.2 H.sub.5                                                                            >300                                            72       H       2-OCH.sub.3   276-278                                         73       H       3-OCH.sub.3   >300                                            74       H       4-OCH.sub.3   >300                                            75       H       2-OC.sub.2 H.sub.5                                                                           273.5-275.0                                     76       H       4-OC.sub.2 H.sub.5                                                                           >300                                            77       H       2-CH.sub.2, 4-OCH.sub.3                                                                       296                                            78       H       2-CH.sub.3, 4-CH.sub.3                                                                       >300                                            79       H       2-CH.sub.3, 5-CH.sub.3                                                                       274.0-276.0                                     80       H       2-CH.sub.3, 6-CH.sub.3                                                                       >300                                            81       H       2-OCH.sub.3, 4-OCH.sub.3                                                                     296.5-298.5                                     82       H       2-OCH.sub.3, 5-OCH.sub.3                                                                     284.5-286.5                                     83       H       3-OCH.sub.2, 5-OCH.sub.3                                                                     300.5-302.0                                     84       H       2-CH.sub.3, 3-Cl                                                                             296.0-297.5                                     85       H       2-CH.sub.3, 4-Cl                                                                             >300                                            86       H       2-CH.sub.3, 5-Cl                                                                             290.5-292.0                                     87       H                                                                                       ##STR17##     304                                            88       H       2-CH(CH.sub.3).sub.2                                                                         239.0-240.0                                     ______________________________________                                    

                                      TABLE 3                                      __________________________________________________________________________      ##STR18##                                                                     Coupler                     Melting Point                                      No.  R.sup.1     (R.sup.2).sub.n                                                                           (°C.)                                       __________________________________________________________________________      89  H           H          228.0-230.0                                         90  H           4-N(CH.sub.3).sub.2                                                                       238.5-240.0                                         91  H           2-OCH.sub.3                                                                               218.0-222.0                                         92  H           3-OCH.sub.3                                                                               186.5-188.5                                         93  H           4-OCH.sub.3                                                                               224.5-225.0                                         94  H           4-OC.sub.2 H.sub.5                                                                        236.0-237.5                                         95  H           2-CH.sub.3 227.0-228.0                                         96  H           3-CH.sub.3 212.5-214.0                                         97  H           4-CH.sub.3 233.0-236.0                                         98  H           2-F        233.0-233.5                                         99  H           3-F        248.5                                              100  H           4-F        239.5-240.0                                        101  H           2-Cl       254.0-255.0                                        102  H           3-Cl       226.5-230.0                                        103  H           4-Cl       265.5-269.0                                        104  H           2-Br       243.0                                              105  H           3-Br       231.0-231.5                                        106  H           4-Br       259.0                                              107  H           2-Cl, 4-Cl 251.5-252.0                                        108  H           3-Cl, 4-Cl 260.0-261.0                                        109  H           2-CN       175.0-176.5                                        110  H           4-CN       267.5-268.0                                        111  H           2-NO.sub.2 240.0                                              112  H           3-NO.sub.2 255.5-257.0                                        113  H           4-NO.sub.2 260.0-261.0                                        114  H           2-CH.sub.3, 4-CH.sub.3                                                                    234.5-236.5                                        115  H           2-OCH.sub.3, 5-OCH.sub.3                                                                  221.5-222.0                                        116  H           2-OCH.sub.3, 3-OCH.sub.3                                                                  191.0-192.0                                                         4-OCH.sub.3                                                   117  CH.sub.3    H          248.5-250.0                                        118                                                                                  ##STR19##  H          182.5-185.0                                        119                                                                                  ##STR20##  H          213.0-214.5                                        120  H                                                                                           ##STR21## 237.0-237.5                                        __________________________________________________________________________

                  TABLE 4                                                          ______________________________________                                          ##STR22##                                                                     Coupler                            Melting                                     No.    R.sup.1 R.sup.2             Point (°C.)                          ______________________________________                                         121    CH.sub.3                                                                               CH.sub.3            232.5-233.0                                 122    H                                                                                       ##STR23##          208.5-209.0                                 123    H                                                                                       ##STR24##          224.0-224.5                                 124    H                                                                                       ##STR25##          197.5-199.0                                 125    H                                                                                       ##STR26##          188.0-188.5                                 126    H                                                                                       ##STR27##          227.0-228.0                                 127    CH.sub.3                                                                                ##STR28##          225.5-226.0                                 128    H                                                                                       ##STR29##          212.5-214.0                                 129    H                                                                                       ##STR30##          257                                         130    H                                                                                       ##STR31##          250                                         131    H                                                                                       ##STR32##          232.5-236.0                                 132    H                                                                                       ##STR33##          240.5-241.5                                 ______________________________________                                    

                  TABLE 5                                                          ______________________________________                                          ##STR34##                                                                     Coupler No. (R).sub.n   Melting Point (°C.)                             ______________________________________                                         133         H           >300                                                   134         2-OCH.sub.3  268                                                   135         3-OCH.sub.3 281.0-283.0                                            136         4-OCH.sub.3  293                                                   137         2-CH.sub.3   297                                                   138         3-CH.sub.3   296                                                   139         4-CH.sub.3  >300                                                   140         4-Cl        >300                                                   141         2-NO.sub.2  >300                                                   142         4-NO.sub.2  >300                                                   143         2-OH        >300                                                   144         2-OH, 3-NO.sub.2                                                                           >300                                                   145         2-OH, 5-NO.sub.2                                                                           >300                                                   146         2-OH, 3-OCH.sub.3                                                                          >300                                                   ______________________________________                                    

                  TABLE 6                                                          ______________________________________                                          ##STR35##                                                                     Coupler No.                                                                               (R).sub.n    Melting Point (°C.)                             ______________________________________                                         147        4-Cl          >300                                                  148        2-NO.sub.2    268-274                                               149        3-NO.sub.2    >300                                                  150        4-NO.sub.2    >300                                                  151                                                                                        ##STR36##     296                                                  152        H             300-307                                               153        2-OCH.sub.3   242-248                                               154        3-OCH.sub.3   269-275                                               155        4-OCH.sub.3    312                                                  156        2-CH.sub.3    265-270                                               157        3-CH.sub.3    270-278                                               158        4-CH.sub.3     304                                                  159        2-Cl          283-288                                               160        3-Cl          281-287                                               ______________________________________                                    

                  TABLE 7                                                          ______________________________________                                          ##STR37##                                                                     Coupler No.                                                                             R.sup.1  (R.sup.2).sub.n                                                                             Melting Point (°C.)                      ______________________________________                                         161      H        2-OCH.sub.3, 4-Cl,                                                                          208.0-208.5                                                       5-CH.sub.3                                                   162      OCH.sub.3                                                                               H            230.5-231.5                                     163      OCH.sub.3                                                                               2-CH.sub.3   205.5-206.0                                     164      OCH.sub.3                                                                               2-OCH.sub.3, 5-OCH.sub.3                                                                    245.5-246.0                                                       4-Cl                                                         ______________________________________                                    

                  TABLE 8                                                          ______________________________________                                          ##STR38##                                                                     Coupler No. X          Melting Point (°C.)                              ______________________________________                                         165                                                                                         ##STR39## 207.0-209.0                                             166                                                                                         ##STR40## 257.0-259.0                                             167                                                                                         ##STR41## 290                                                     ______________________________________                                    

                  TABLE 9                                                          ______________________________________                                          ##STR42##                                                                     Coupler                                                                        No.    R.sup.1             Melting Point (°C.)                          ______________________________________                                         168                                                                                    ##STR43##          >300                                                169                                                                                    ##STR44##          >300                                                170                                                                                    ##STR45##          >300                                                171                                                                                    ##STR46##           298                                                ______________________________________                                    

                                      TABLE 10                                     __________________________________________________________________________      ##STR47##                                                                     Coupler                                                                        No.  X      R             Melting Point (°C.)                           __________________________________________________________________________     172                                                                                  ##STR48##                                                                             ##STR49##    180-183                                              173                                                                                  ##STR50##                                                                             ##STR51##    228.5-229.5                                          174                                                                                  ##STR52##                                                                             ##STR53##    >262                                                 175                                                                                  ##STR54##                                                                             ##STR55##    226.5-227.0                                          176                                                                                  ##STR56##                                                                             ##STR57##    308-310                                              177                                                                                  ##STR58##                                                                             ##STR59##    222-223                                              __________________________________________________________________________

                                      TABLE 11                                     __________________________________________________________________________      ##STR60##                                                                     Coupler No.                                                                           R.sup.1                                                                             R.sup.2       Melting Point (°C.)                           __________________________________________________________________________     178    H    H             220.5-221.5                                          179    CH.sub.3                                                                            H             190.5-192.5                                          180    CH.sub.3                                                                            CH.sub.3      196.0-198.0                                          181    H                                                                                    ##STR61##    222.0-223.0                                          __________________________________________________________________________

                                      TABLE 12                                     __________________________________________________________________________     Coupler                         Melting Point                                  No.  Formula                    (°C.)                                   __________________________________________________________________________     182                                                                                  ##STR62##                 >300                                           183                                                                                  ##STR63##                 >300                                           184                                                                                  ##STR64##                 >300                                           185                                                                                  ##STR65##                 >300                                           186                                                                                  ##STR66##                 >300                                           187                                                                                  ##STR67##                 >300                                           188                                                                                  ##STR68##                 122.0-122.5                                    189                                                                                  ##STR69##                 222.5-224.0                                    190                                                                                  ##STR70##                 74.5-75.5                                      191                                                                                  ##STR71##                 275.5-276.5                                    192                                                                                  ##STR72##                 130.5-131.5                                    193                                                                                  ##STR73##                 >300                                           194                                                                                  ##STR74##                 >300                                           195                                                                                  ##STR75##                 >300                                           196                                                                                  ##STR76##                 172.5-173.5                                    197                                                                                  ##STR77##                 262.5-265.5                                    198                                                                                  ##STR78##                 >300                                           199                                                                                  ##STR79##                 >300                                           200                                                                                  ##STR80##                 128.0-129.0                                    __________________________________________________________________________

                  TABLE 13                                                         ______________________________________                                          ##STR81##                                                                     Coupler No.                                                                             R.sup.1   (R.sup.2).sub.n                                                                           Melting Point (°C.)                       ______________________________________                                         201      Cl        H          >300                                             202      Cl        2-OCH.sub.3                                                                               >300                                             203      Cl        3-OCH.sub.3                                                                               >300                                             204      Cl        4-OCH.sub.3                                                                               >300                                             205      Cl        2-CH.sub.3 >300                                             206      Cl        3-CH.sub.3 >300                                             207      Cl        4-CH.sub.3 >300                                             208      Cl        2-Cl       >300                                             209      Cl        3-Cl       >300                                             210      Cl        4-Cl       >300                                             211      Cl        2-NO.sub.2 >300                                             212      Cl        3-NO.sub.2 >300                                             213      Cl        4-NO.sub.2 >300                                             214      Cl        2-CH.sub.3, 4-Cl                                                                          >300                                             215      Cl        2-CH.sub.3, 4-CH.sub.3                                                                    >300                                             216      Cl        2-C.sub.2 H.sub.5                                                                         299.0-301.0                                      217      CH.sub.3  H          >300                                             218      CH.sub.3  2-OCH.sub.3                                                                                 297                                            219      CH.sub.3  3-OCH.sub.3                                                                               >300                                             220      CH.sub.3  4-OCH.sub.3                                                                               >300                                             221      CH.sub.3  2-CH.sub.3 >300                                             222      CH.sub.3  3-CH.sub.3 >300                                             223      CH.sub.3  4-CH.sub.3 >300                                             224      CH.sub.3  2-Cl       >300                                             225      CH.sub.3  3-Cl       >300                                             226      CH.sub.3  4-Cl       >300                                             227      CH.sub.3  2-NO.sub.2 >300                                             228      CH.sub.3  3-NO.sub.2 >300                                             229      CH.sub.3  4-NO.sub.2 >300                                             230      CH.sub.3  2-CH.sub.3, 4-Cl                                                                          >300                                             231      CH.sub.3  2-CH.sub.3, 4-CH.sub.3                                                                    >300                                             232      CH.sub.3  2-C.sub.2 H.sub.5                                                                         268.5-270.0                                      233      OCH.sub.3 H           289.0                                           234      OCH.sub.3 2-OCH.sub.3                                                                               268.0-270.0                                      235      OCH.sub.3 3-OCH.sub.3                                                                               >300                                             236      OCH.sub.3 4-OCH.sub.3                                                                               >300                                             237      OCH.sub.3 2-CH.sub.3 284.5-285.5                                      238      OCH.sub.3 3-CH.sub.3 >300                                             239      OCH.sub.3 4-CH.sub.3 >300                                             240      OCH.sub.3 3-Cl       >300                                             242      OCH.sub.3 4-Cl       >300                                             243      OCH.sub.3 2-NO.sub.2 >300                                             244      OCH.sub.3 3-NO.sub.2 >300                                             245      OCH.sub.3 4-NO.sub.2 >300                                             246      OCH.sub.3 2-C.sub.2 H.sub.5                                                                         264.5-266.5                                      ______________________________________                                    

                  TABLE 14                                                         ______________________________________                                         Coupler No.                                                                               Formula                                                             ______________________________________                                         247                                                                                        ##STR82##                                                          248                                                                                        ##STR83##                                                          249                                                                                        ##STR84##                                                          250                                                                                        ##STR85##                                                          251                                                                                        ##STR86##                                                          252                                                                                        ##STR87##                                                          253                                                                                        ##STR88##                                                          254                                                                                        ##STR89##                                                          255                                                                                        ##STR90##                                                          256                                                                                        ##STR91##                                                          257                                                                                        ##STR92##                                                          258                                                                                        ##STR93##                                                          ______________________________________                                    

                  TABLE 15                                                         ______________________________________                                          ##STR94##                                                                     Coupler No.    (R.sup.2).sub.n                                                 ______________________________________                                         259            2-Cl, 3-Cl                                                      260            2-Cl, 4-Cl                                                      261            3-Cl, 5-Cl                                                      ______________________________________                                    

                  TABLE 16                                                         ______________________________________                                          ##STR95##                                                                     Coupler No.    (R.sup.2).sub.n                                                 ______________________________________                                         262            4-CH.sub.2                                                      263            3-NO.sub.2                                                      264            2-Cl                                                            265            3-Cl                                                            266            4-Cl                                                            267            2-Cl, 3-Cl                                                      268            2-Cl, 4-Cl,                                                     269            3-Cl, 5-Cl                                                      270            2-Cl, 5-Cl                                                      271            3-Cl, 4-Cl                                                      ______________________________________                                    

In the electrophotographic photoconductor of the present invention, disazo pigments of formula (11) and formula (12) are particularly preferable because of their high sensitivities in the visible light range: ##STR96##

When any of these disazo pigments of formulas (11) and (12) and the trisazo pigment of the previously mentioned formula (2) are mixed and pulverized simultaneously, a pigment dispersion coating liquid with excellent stability can be obtained. Therefore, a photoconductive layer with an increased sensitizing effect can be formed by coating the above pigment dispersion coating liquid.

As the trisazo pigment of formula (2), the following compound of formula (13) is preferably employed in the present invention: ##STR97## wherein R³¹ to R³⁹ each is hydrogen, --CH₃, --C₂ H₅, --C₃ H₇, chlorine, fluorine, iodine, bromine, CH₃ --, C₂ H₅ O--, C₃ H₇ O--, --NO₂, --CN, --CF₃ or --OH.

The trisazo compound of formula (13) can generate electric charges very efficiently, particularly by the application of light with a wavelength of 700 nm or more in the near infrared region. When the trisazo compound of formula (13) is simultaneously pulverized with the above-mentioned disazo pigments of formulas (11) or (12) and the thus obtained mixture is contained in a single-layered photoconductive layer, the photosensitivity of the obtained photoconductor becomes sufficiently high in a broad range from the visible light range to the near infrared range.

In particular, to prepare a photoconductor with a high sensitivity to the LD light of 780 to 850 nm, the following trisazo pigments of formulas (13-a) and (13-b) are advantageous because they have high sensitivities in a board wave range up to 850 nm: ##STR98##

In the electrophotographic photoconductor of the present invention, oxazole derivatives, imidazole derivatives and triphenylamine derivatives can be used as charge transporting materials.

Further, it is preferable that the charge transporting material for use in the present invention be a positive hole transporting material which is selected from the group consisting of the following compounds of formulas (14) to (32): ##STR99## wherein R¹ is methyl group, ethyl group, 2-hydroxyethyl group or 2-chloroethyl group; R² is methyl group, ethyl group, benzyl group or phenyl group; and R³ is hydrogen, chlorine, bromine, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a dialkylamino group, or nitro group; ##STR100## wherein Ar is naphthalene ring, anthracene ring, styryl ring, each of which may have a substituent, pyridyl ring, furan ring, or thiophene ring; and R is an alkyl group or benzyl group; ##STR101## wherein R¹ is an alkyl group, benzyl group, phenyl group, or naphthyl group; R² is hydrogen, an alkyl group having 1 to 3 carbon atoms, an alkoxyl group having 1 to 3 carbon atoms, a dialkylamino group, a diaralkylamino group or a diarylamino group; n is an integer of 1 to 4; when n is 2 or more, R² may be the same or different; and R³ is hydrogen or methoxy group; ##STR102## wherein R¹ is an alkyl group having 1 to 11 carbon atoms, a substituted or unsubstituted phenyl group, or a heterocyclic ring; R² and R³ may be the same or different and each is hydrogen, an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group, a chloroalkyl group, or a substituted or unsubstituted aralkyl group, and R² and R³ may form a nitrogen-containing heterocyclic ring in combination; and R⁴ is hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group, or a halogen atom, and may be the same or different; ##STR103## wherein R¹ is hydrogen, a substituted or unsubstituted alkyl group, or phenyl group; R² is hydrogen, a substituted or unsubstituted alkyl group, an alkoxyl group or a halogen atom; ##STR104## wherein R is hydrogen or a halogen atom; Ar is phenyl group, naphthyl group, anthryl group or carbazolyl group, each of which may have a substituent; ##STR105## wherein R¹ is hydrogen, a halogen atom, cyano group, an alkoxyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms; and Ar is ##STR106## wherein R² is an alkyl group having 1 to 4 carbon atoms; R³ is hydrogen, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, or a dialkylamino group; n is an integer of 1 or 2; when n is 2, R³ may be the same or different; and R⁴ and R⁵ each is hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted benzyl group; ##STR107## wherein R is carbazolyl group, pyridyl group, thienyl group, indolyl group, furyl group, a substituted or unsubstituted phenyl group, styryl group, naphthyl group, or anthryl group, each of which may have a substituent selected from the group consisting of a dialkylamino group, an alkyl group, an alkoxyl group, carboxyl group or an ester group thereof, a halogen atom, cyano group, an aralkylamino group, an N-alkyl-N-aralkylamino group, amino group, nitro group and acetylamino group; ##STR108## wherein R¹ is a lower alkyl group, a substituted or unsubstituted phenyl group, or benzyl group; R² and R³ each is hydrogen, a lower alkyl group, a lower alkoxyl group, a halogen atom, nitro group, or an amino group which may have as a substituent a lower alkyl group or benzyl group; and n is an integer of 1 or 2; ##STR109## wherein R¹ is hydrogen, an alkyl group, an alkoxyl group or a halogen atom; R² and R³ each is an alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group; R⁴ is hydrogen, a lower alkyl group, or a substituted or unsubstituted phenyl group; and Ar is a substituted or unsubstituted phenyl group or naphthyl group; ##STR110## wherein n is an integer of 0 or 1; R¹ is hydrogen, an alkyl group or a substituted or unsubstituted phenyl group; Ar¹ is a substituted or unsubstituted aryl group; R⁵ is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; and A is ##STR111## 9-anthryl group or a substituted or unsubstituted N-alkylcarbazolyl group, in which R² is hydrogen, an alkyl group, an alkoxyl group, a halogen atom, or ##STR112## in which R³ and R⁴ each is an alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group, and R³ and R⁴ may be the same or different and may form a ring in combination; m is an integer of 0 to 3; and when m is 2 or more, R² may be the same or different; and when n is 0, A and R¹ may form a ring in combination; ##STR113## wherein R¹, R² and R³ each is hydrogen, a lower alkyl group, a lower alkoxyl group, a dialkylamino group or a halogen atom; and n is an integer of 0 or 1; ##STR114## wherein R¹ and R² each is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; and A is a substituted amino group, a substituted or unsubstituted aryl group, or an allyl group; ##STR115## wherein X is hydrogen, a lower alkyl group, or a halogen atom; R is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; and A is a substituted amino group, or a substituted or unsubstituted aryl group; ##STR116## wherein R¹ is a lower alkyl group, a lower alkoxyl group, or a halogen atom; n is an integer of 0 to 4; and R² and R³ may be the same or different, and each is hydrogen, a lower alkyl group, a lower alkoxyl group, or a halogen atom; ##STR117## wherein R¹, R³ and R⁴ each is hydrogen, an amino group, a thioalkoxyl group, an aryloxy group, methylenedioxy group, a substituted or unsubstituted alkyl group, a halogen atom, or a substituted or unsubstituted aryl group; R² is hydrogen, an alkoxyl group, a substituted or unsubstituted alkyl group, or a halogen atom, provided that not all of R¹, R², R³, and R⁴ are hydrogen at the same time; k, l, m and n each is an integer of 1 to 4, and when each of k, l, m and n is 2, 3 or 4, R¹, R², R³, and R⁴ may be the same or different; ##STR118## wherein Ar is a condensed polycyclic hydrocarbon group having 18 or less carbon atoms; R¹ and R² may be the same or different, and each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxyl group, or a substituted or unsubstituted phenyl group;

    A--CH═CH--Ar--CH═CH--A                             (31)

wherein Ar is a substituted or unsubstituted aromatic hydrocarbon group; and A is ##STR119## in which Ar' is a substituted or unsubstituted aromatic hydrocarbon group; and R¹ and R² each is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; and ##STR120## wherein Ar is an aromatic hydrocarbon group; R is hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; and n is an integer of 0 or 1, and m is an integer of 1 or 2, and when n=0 and m=1, Ar and R may form a ring in combination.

Specific examples of the compound of formula (14) are 9-ethylcarbazole-3-aldehyde-1-methyl-1-phenylhydrazone, 9-ethylcarbazole-3-aldehyde-1-benzyl-1-phenylhydrazone, and 9-ethylcarbazole-3-aldehyde-1,1-diphenylhydrazone.

Specific examples of the compound of formula (15) are 4-diethylaminostyryl-β-aldehyde-1-methyl-1-phenylhydrazone, and 4-methyoxynaphthalene-1-aldehyde-1-benzyl-1-phenylhydrazone.

Specific examples of the compound of formula (16) are 4-methoxybenzaldehyde-1-methyl-1-phenylhydrazone, 2,4-dimethoxybenzaldehyde-1-benzyl-1-phenylhydrazone, 4-diethylaminobenzaldehyde-1,1-diphenylhydrazone, 4-methoxybenzaldehyde-1-benzyl-1-(4-methoxy)phenylhydrazone, 4-diphenylaminobenzaldehyde-1-benzyl-1-phenylhydrazone, and 4-dibenzylaminobenzaldehyde-1,1-diphenylhydrazone.

Specific examples of the compound of formula (17) are 1,1-bis(4-dibenzylaminophenyl)propane, tris(4-diethylaminophenyl)methane, 1,1-bis(4-dibenzylaminophenyl)propane, and 2,2'-dimethyl-4,4'-bis(diethylamino)triphenylmethane.

As the compound of formula (18), N-ethyl-3,6-tetrabenzylaminocarbazole can be employed.

Specific examples of the compound of formula (19) are 9-(4-diethylaminostyryl)anthracene, and 9-bromo-10-(4-diethylaminostyryl)anthracene.

Specific examples of the compound of formula (20) are 9-(4-dimethylaminobenzylidene)fluorene, and 3-(9-fluorenylidene)-9-ethylcarbazole.

Specific examples of the compound of formula (21) are 1,2-bis(4-diethylaminostyryl)benzene, and 1,2-bis(2,4-dimethoxystyryl)benzene.

Specific examples of the compound of formula (22) are 3-styryl-9-ethylcarbazole, and 3-(4-methoxystyryl)-9-ethylcarbazole.

Specific examples of the compound of formula (23) are 4-diphenylaminostilbene, 4-dibenzylaminostilbene, 4-ditolyllaminostilbene, 1-(4-diphenylaminostyryl)naphthalene, and 1-(4-diethylaminostyryl)naphthalene.

Specific examples of the compound of formula (24) are 4'-diphenylamino-α-phenylstilbene, and 4'-bis(methylphenyl)amino-α-phenylstilbene.

Specific examples of the compound of formula (25) are 1-phenyl-3-(4-diethylaminostyryl)-5-(4-diethylaminophenyl)pyrazoline, and 1-phenyl-3-(4-dimethylaminostyryl)-5-(4-dimethylaminophenyl)pyrazoline.

Specific examples of the compound of formula (26) are 2,5-bis(4-diethylaminophenyl)-1,3,4-oxadiazole, 2-N,N-diphenylamino-5-(4-diethylaminophenyl)-1,3,4-oxadiazole, and 2-(4-dimethylaminophenyl)-5-(4-diethylaminophenyl)-1,3,4-oxadiazole.

Specific examples of the compound of formula (27) are 2-N,N-diphenylamino-5-(N-ethylcarbazole-3-yl)-1,3,4-oxadiazole, and 2-(4-diethylaminophenyl)-5-(N-ethylcarbazole-3-yl)-1,3,4-oxadiazole.

Specific examples of the compound of formula (28) are N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1'-bisphenyl]-4,4'-diamine, and 3,3'-dimethyl-N,N,N',N'-tetrakis(4-methylphenyl)-[1,1'-biphenyl]-diamine.

Specific examples of the biphenylamine compound of formula (29) are 4'-methoxy-N,N-diphenyl-[1,1'-biphenyl]-4-amine, 4'-methyl-N,N'-bis(4-methylphenyl)-[1,1'-biphenyl]-4-amine, and 4'-methoxy-N,N'-bis(4-methylphenyl)-[1,1'-biphenyl]-4-amine.

Specific examples of the triarylamine compound of formula (30) are 1-phenylaminopyrene, and 1-di(p-tolylamino)pyrene.

Specific examples of the diolefin aromatic compound of formula (31) are 1,4-bis(4-diphenylaminostyryl)benzene, and 1,4-bis[4-di(p-tolyl)aminostyryl]benzene.

Specific examples of the styrylpyrene compound of formula (32) are 1-(4-diphenylaminostyryl)pyrene, and 1-[4-di(p-tolyl)aminostyryl]pyrene.

These charge transporting materials may be used alone or in combination.

It is preferable that the charge transporting material for use in the present invention have an oxidation potential of +0.5 V (vs SCE) or more. In particular, the charge transporting materials of formulas (14), (15), (17), (19), (22), (23), (24), (28), (29), (30) and (31) are preferable from the viewpoints of charging characteristics and photosensitivity of the obtained photoconductor. In particular, an electrophotographic photoconductor employing the positive hole transporting compound of formula (17) is superior to others in the charging stability when repeatedly used in electrophotographic process.

The oxidation potential of the charge transporting material for use in the present invention means a half-wave potential obtained by conventionally known cyclic voltametry, using acetonitrile as a solvent, 0.1 MTEAP as an electrolyte, and a saturated calomel electrode (SCE) as a reference electrode.

The charge transporting material for use in the electrophotographic photoconductor of the present invention may comprise the above-mentioned organic positive hole transporting material and an organic acceptor compound.

Any conventional organic acceptor compounds can be employed in the present invention. Particularly, it is preferable to use organic acceptor compounds of formulas (1) to (14) in combination:

[Organic Acceptor Compound of Formula (1)] ##STR121## wherein R¹ is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, an alkoxycarbonyl group, an N-alkylcarbamoyl group, cyano group or nitro group; n is an integer of 1 to 3; X is ##STR122## in which R² and R³ each is an alkyl group, and R³ may be bonded to each other. [Organic Acceptor Compound of Formula (2)] ##STR123## wherein Ar is a substituted or unsubstituted aromatic group; and X is cyano group or an alkoxycarbonyl group. [Organic Acceptor Compound of Formula (3)]

    Ar--CH═C(COOR).sub.2                                   (3)

wherein Ar is a substituted or unsubstituted aromatic group; and R is an alkyl group, and R may be bonded to each other to form a ring.

[Organic Acceptor Compound of Formula (4)] ##STR124## wherein X is sulfur or selenium; Y is a substituted or unsubstituted alkyl group, an aryl group, or cyano group; R is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, cyano group, nitro group, a halogen atom, or hydrogen; and n is an integer of 1 to 3. [Organic Acceptor Compound of Formula (5)]

    Ar--CH═CHNO.sub.2                                      (5)

wherein Ar is a substituted or unsubstituted aromatic group.

[Organic Acceptor Compound of Formula (6)] ##STR125## wherein R¹ and R² each is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a heterocyclic aromatic group. [Organic Acceptor Compound of Formula (7)] ##STR126## wherein R¹ is hydrogen, a halogen atom, an alkyl group, or a substituted or unsubstituted phenyl group; R² is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, a halogen atom, an alkoxycarbonyl group, an N-alkylcarbamoyl group, cyano group, or nitro group; and n is an integer of 1 to 3. [Organic Acceptor Compound of Formula (8)] ##STR127## wherein R³ is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, a halogen atom, an alkoxycarbonyl group, an N-alkylcarbamoyl group, cyano group, or nitro group; and n is an integer of 1 to 3. [Organic Acceptor Compound of Formula (9)] ##STR128## wherein R¹ and R² each is a substituted or unsubstituted phenyl group, a substituted or unsubstituted polycyclic aromatic group, or a substituted or unsubstituted heterocyclic group. [Organic Acceptor Compound (10)] ##STR129## wherein R¹ and R² each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, an N-alkylcarbamoyl group, an alkylcarbonyl group, an arylcarbonyl group, cyano group, nitro group, an alkoxyl group, an aryloxy group, an amino group, or a vinyl group of ##STR130## in which X is hydrogen or an alkyl group, and at least one of Y or Z is a substituted or unsubstituted phenyl group and the other is hydrogen; and n and m each is an integer of 1 to 3. [Organic Acceptor Compound of Formula (11)] ##STR131## wherein R³ and R⁴ each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, an N-alkylcarbamoyl group, an alkylcarbonyl group, an arylcarbonyl group, cyano group, nitro group, an alkoxyl group, an aryloxy group, an amino group, or a vinyl group of ##STR132## in which X is hydrogen or an alkyl group, and at least one of Y or Z is a substituted or unsubstituted phenyl group and the other is hydrogen; and n and m each is an integer of 1 to 3. [Organic Acceptor Compound of Formula (12)] ##STR133## wherein R⁵ and R⁶ each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, an N-alkylcarbamoyl group, an alkylcarbonyl group, an arylcarbonyl group, cyano group, nitro group, an alkoxyl group, an aryloxy group an amino group, or a vinyl group of ##STR134## in which X is hydrogen or an alkyl group, and at least one of Y or Z is a substituted or unsubstituted phenyl group and the other is hydrogen; and n and m each is an integer of 1 to 3. [Organic Acceptor Compound of Formula (13)] ##STR135## wherein R⁷ and R⁸ each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, an N-alkylcarbamoyl group, an alkylcarbonyl group, an arylcarbonyl group, cyano group, nitro group, an alkoxyl group, an aryloxy group, an amino group, or a vinyl group of ##STR136## in which X is hydrogen or an alkyl group, and at least one of Y or Z is a substituted or unsubstituted phenyl group and the other is hydrogen; and n and m each is an integer of 1 to 3. [Organic Acceptor Compound of Formula (14)] ##STR137## wherein X is O or N--R, in which R is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

TABLES 17-30 respectively show specific examples of the organic acceptor compound of formulae (1) to (14).

                  TABLE 17                                                         ______________________________________                                          ##STR138##                    (1)                                             Compound No.                                                                               X               R.sup.1                                            ______________________________________                                          1          C(CN).sub.2     4'-NO.sub.2                                         2          C(CN).sub.2     3'-NO.sub.2                                         3          C(CN).sub.2     3'-NO.sub.2 -4'-Cl                                  4          C(CN).sub.2     4'-CN                                               5          C(CN).sub.2     4'-Cl                                               6          C(CN).sub.2     4'-COOC.sub.2 H.sub.5                               7          C(CN).sub.2     4'-COOC.sub.4 H.sub.9                               8          C(CN).sub.2     4'-CF.sub.3                                         9          C(CN).sub.2     4'-C.sub.4 H.sub.9                                 10                                                                                          ##STR139##     4'-NO.sub.2                                        11                                                                                          ##STR140##     3'-NO.sub.2 -4'-Cl                                 12                                                                                          ##STR141##     3'-NO.sub.2 -4'-CH.sub.3                           13                                                                                          ##STR142##     4'-CN                                              14                                                                                          ##STR143##     4'-Cl                                              15                                                                                          ##STR144##     4'-COOCH.sub.2 H.sub.5                             16                                                                                          ##STR145##     4'-CF.sub.3                                        17                                                                                          ##STR146##     4'-C.sub.4 H.sub.9                                 18                                                                                          ##STR147##     4'-NO.sub.2                                        19                                                                                          ##STR148##     3'-NO.sub.2                                        20                                                                                          ##STR149##     3'-NO.sub.2, 4'-Cl                                 21                                                                                          ##STR150##     3'-NO.sub.2, 4'-CH.sub.3                           22                                                                                          ##STR151##     4'-CN                                              23                                                                                          ##STR152##     3'-CF.sub.3, 4'-CN                                 24                                                                                          ##STR153##     4'-Cl                                              25                                                                                          ##STR154##     4'-COOC.sub.2 H.sub.5                              26                                                                                          ##STR155##     4'-COOC.sub.4 H.sub.9                              27                                                                                          ##STR156##     4'-CON(C.sub.4 H.sub.9).sub.2                      28                                                                                          ##STR157##     4'-CF.sub.3                                        29                                                                                          ##STR158##     4'-C.sub.2 H.sub.5                                 30                                                                                          ##STR159##     4'-C.sub.4 H.sub.9                                 31          C(COOCH.sub.3).sub.2                                                                           4'-NO.sub.2                                        32          C(COOCH.sub.3).sub.2                                                                           4'-Cl                                              33          C(COOCH.sub.3).sub.2                                                                           4'-COOC.sub.4 H.sub.9                              34          C(COOCH.sub.3).sub.2                                                                           4'-CF.sub.3                                        35          C(COOCH.sub.3).sub.2                                                                           4'-C.sub.4 H.sub.9                                 36          C(COOC.sub.4 H.sub.9).sub.2                                                                    4'-NO.sub.2                                        37          C(COOC.sub.4 H.sub.9).sub.2                                                                    2'-CH.sub.3, 4'-NO.sub.2                           38          C(COOC.sub.4 H.sub.9).sub.2                                                                    3'-NO.sub.2, 4'-Cl                                 39          C(COOC.sub.4 H.sub.9).sub.2                                                                    3'-NO.sub.2, 4'-CH.sub.3                           40          C(COOC.sub.4 H.sub.9).sub.2                                                                    4'-CN                                              41          C(COOC.sub.4 H.sub.9).sub.2                                                                    4'-Cl                                              42          C(COOC.sub.4 H.sub.9).sub.2                                                                    4'-COOC.sub.4 H.sub.9                              43          C(COOC.sub.4 H.sub.9).sub.2                                                                    4'-CF.sub.3                                        44          C(COOC.sub.4 H.sub.9).sub.2                                                                    4'-C.sub.4 H.sub.9                                 45                                                                                          ##STR160##     4'-NO.sub.2                                        46                                                                                          ##STR161##     2'-CH.sub.3 -4'-NO.sub.2                           47                                                                                          ##STR162##     4'-CN                                              48                                                                                          ##STR163##     4'-Cl                                              49                                                                                          ##STR164##     4'-COOC.sub.2 H.sub.5                              50                                                                                          ##STR165##     4'-COOC.sub.4 H.sub.9                              51                                                                                          ##STR166##     4'-CF.sub.3                                        52                                                                                          ##STR167##     4'-C.sub.2 H.sub.5                                 53                                                                                          ##STR168##     4'-C.sub.4 H.sub.9                                 ______________________________________                                    

                                      TABLE 18                                     __________________________________________________________________________      ##STR169##                  (2)                                               Compound No.                                                                           X          Ar                                                          __________________________________________________________________________      1      CN                                                                                         ##STR170##                                                  2      CN                                                                                         ##STR171##                                                  3      CN                                                                                         ##STR172##                                                  4      CN                                                                                         ##STR173##                                                  5      CN                                                                                         ##STR174##                                                  6      CN                                                                                         ##STR175##                                                  7      CN                                                                                         ##STR176##                                                  8      CN                                                                                         ##STR177##                                                  9      CN                                                                                         ##STR178##                                                 10      CN                                                                                         ##STR179##                                                 11      CN                                                                                         ##STR180##                                                 12      CN                                                                                         ##STR181##                                                 13      CN                                                                                         ##STR182##                                                 14      CN                                                                                         ##STR183##                                                 15      CN                                                                                         ##STR184##                                                 16      CN                                                                                         ##STR185##                                                 17      CN                                                                                         ##STR186##                                                 18      CN                                                                                         ##STR187##                                                 19      CN                                                                                         ##STR188##                                                 20      CN                                                                                         ##STR189##                                                 21      CN                                                                                         ##STR190##                                                 22      CN                                                                                         ##STR191##                                                 23      CN                                                                                         ##STR192##                                                 24      CN                                                                                         ##STR193##                                                 25      CN                                                                                         ##STR194##                                                 26      CN                                                                                         ##STR195##                                                 27      CN                                                                                         ##STR196##                                                 28      CN                                                                                         ##STR197##                                                 29      CN                                                                                         ##STR198##                                                 30      CN                                                                                         ##STR199##                                                 31      CN                                                                                         ##STR200##                                                 32      CN                                                                                         ##STR201##                                                 33      CN                                                                                         ##STR202##                                                 34      CN                                                                                         ##STR203##                                                 35      CN                                                                                         ##STR204##                                                 36      CN                                                                                         ##STR205##                                                 37      COOC.sub.2 H.sub.5                                                                         ##STR206##                                                 38      COOC.sub.2 H.sub.5                                                                         ##STR207##                                                 39      COOC.sub.2 H.sub.5                                                                         ##STR208##                                                 40      COOC.sub.2 H.sub.5                                                                         ##STR209##                                                 41      COOC.sub.2 H.sub.5                                                                         ##STR210##                                                 42      COOC.sub.2 H.sub.5                                                                         ##STR211##                                                 43      COOC.sub.2 H.sub.5                                                                         ##STR212##                                                 44      COOC.sub.2 H.sub.5                                                                         ##STR213##                                                 45      COOC.sub.2 H.sub.5                                                                         ##STR214##                                                 46      COOC.sub.2 H.sub.5                                                                         ##STR215##                                                 47      COOC.sub.2 H.sub.5                                                                         ##STR216##                                                 48      COOC.sub.2 H.sub.5                                                                         ##STR217##                                                 49      COOC.sub.2 H.sub.5                                                                         ##STR218##                                                 50      COOC.sub.2 H.sub.5                                                                         ##STR219##                                                 51      COOC.sub.2 H.sub.5                                                                         ##STR220##                                                 52      COOC.sub.2 H.sub.5                                                                         ##STR221##                                                 53      COOC.sub.2 H.sub.5                                                                         ##STR222##                                                 54      COOC.sub.4 H.sub.9                                                                         ##STR223##                                                 55      COOC.sub.4 H.sub.9                                                                         ##STR224##                                                 56      COOC.sub.4 H.sub.9                                                                         ##STR225##                                                 57      COOC.sub.4 H.sub.9                                                                         ##STR226##                                                 58      COOC.sub.4 H.sub.9                                                                         ##STR227##                                                 59      COOC.sub.4 H.sub.9                                                                         ##STR228##                                                 60      COOC.sub.4 H.sub.9                                                                         ##STR229##                                                 61      COOC.sub.4 H.sub.9                                                                         ##STR230##                                                 62      COOC.sub.4 H.sub.9                                                                         ##STR231##                                                 63      COOC.sub.4 H.sub.9                                                                         ##STR232##                                                 64      COOC.sub.4 H.sub.9                                                                         ##STR233##                                                 65      COOC.sub.4 H.sub.9                                                                         ##STR234##                                                 66      COOC.sub.4 H.sub.9                                                                         ##STR235##                                                 67      COOC.sub.4 H.sub.9                                                                         ##STR236##                                                 68      COOC.sub.4 H.sub.9                                                                         ##STR237##                                                 69      COOC.sub.4 H.sub.9                                                                         ##STR238##                                                 70      COOC.sub.4 H.sub.9                                                                         ##STR239##                                                 71      COOC.sub.4 H.sub.9                                                                         ##STR240##                                                 72      COOC.sub.4 H.sub.9                                                                         ##STR241##                                                 73      COOC.sub.4 H.sub.9                                                                         ##STR242##                                                 74      COOC.sub.4 H.sub.9                                                                         ##STR243##                                                 75      COOC.sub.4 H.sub.9                                                                         ##STR244##                                                 76      COOC.sub.4 H.sub.9                                                                         ##STR245##                                                 77      COOC.sub.4 H.sub.9                                                                         ##STR246##                                                 78      COOC.sub.4 H.sub.9                                                                         ##STR247##                                                 79      COOC.sub.4 H.sub.9                                                                         ##STR248##                                                 80      COOC.sub.4 H.sub.9                                                                         ##STR249##                                                 81      COOC.sub.4 H.sub.9                                                                         ##STR250##                                                 82      COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR251##                                                 83      COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR252##                                                 84      COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR253##                                                 85      COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR254##                                                 86      COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR255##                                                 87      COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR256##                                                 88      COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR257##                                                 89      COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR258##                                                 90      COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR259##                                                 91      COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR260##                                                 92      COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR261##                                                 93      COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR262##                                                 94      COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR263##                                                 95      COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR264##                                                 96      COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR265##                                                 97      COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR266##                                                 98      COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR267##                                                 99      COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR268##                                                 100     COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR269##                                                 101     COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR270##                                                 102     COOCH.sub.2 CH(CH.sub.3).sub.2                                                             ##STR271##                                                 103     COOC.sub.3 H.sub.7                                                                         ##STR272##                                                 104     COOC.sub.3 H.sub.7                                                                         ##STR273##                                                 105     COOC.sub.3 H.sub.7                                                                         ##STR274##                                                 106     COOC.sub.3 H.sub.7                                                                         ##STR275##                                                 107     COOC.sub.3 H.sub.7                                                                         ##STR276##                                                 108     COOC.sub.3 H.sub.7                                                                         ##STR277##                                                 109     COOC.sub.3 H.sub.7                                                                         ##STR278##                                                 110     COOC.sub.3 H.sub.7                                                                         ##STR279##                                                 111     COOC.sub.3 H.sub.7                                                                         ##STR280##                                                 112     COOC.sub.3 H.sub.7                                                                         ##STR281##                                                 113     COOC.sub.3 H.sub.7                                                                         ##STR282##                                                 114     COOC.sub.3 H.sub.7                                                                         ##STR283##                                                 115     COOC.sub.3 H.sub.7                                                                         ##STR284##                                                 116     COOC.sub.3 H.sub.7                                                                         ##STR285##                                                 117     COOC.sub.3 H.sub.7                                                                         ##STR286##                                                 118     COOC.sub.3 H.sub.7                                                                         ##STR287##                                                 119     COOC.sub.3 H.sub.7                                                                         ##STR288##                                                 120     COOC.sub.3 H.sub.7                                                                         ##STR289##                                                 121     COOC.sub.3 H.sub.7                                                                         ##STR290##                                                 122     COOC.sub.3 H.sub.7                                                                         ##STR291##                                                 123     COOC.sub.3 H.sub.7                                                                         ##STR292##                                                 124     COOC.sub.3 H.sub.7                                                                         ##STR293##                                                 125     COOC.sub.3 H.sub.7                                                                         ##STR294##                                                 126     COOCH(CH.sub.3).sub.2                                                                      ##STR295##                                                 127     COOCH(CH.sub.3).sub.2                                                                      ##STR296##                                                 128     COOCH(CH.sub.3).sub.2                                                                      ##STR297##                                                 129     COOCH(CH.sub.3).sub.2                                                                      ##STR298##                                                 130     COOCH(CH.sub.3).sub.2                                                                      ##STR299##                                                 131     COOCH(CH.sub.3).sub.2                                                                      ##STR300##                                                 132     COOCH(CH.sub.3).sub.2                                                                      ##STR301##                                                 133     COOCH(CH.sub.3).sub.2                                                                      ##STR302##                                                 134     COOCH(CH.sub.3).sub.2                                                                      ##STR303##                                                 135     COOCH(CH.sub.3).sub.2                                                                      ##STR304##                                                 136     COOCH(CH.sub.3).sub.2                                                                      ##STR305##                                                 137     COOCH(CH.sub.3).sub.2                                                                      ##STR306##                                                 138     COOCH(CH.sub.3).sub.2                                                                      ##STR307##                                                 139     COOCH(CH.sub.3).sub.2                                                                      ##STR308##                                                 140     COOCH(CH.sub.3).sub.2                                                                      ##STR309##                                                 141     COOCH(CH.sub.3).sub.2                                                                      ##STR310##                                                 142     COOCH(CH.sub.3).sub.2                                                                      ##STR311##                                                 143     COOCH(CH.sub.3).sub.2                                                                      ##STR312##                                                 144     COOCH(CH.sub.3).sub.2                                                                      ##STR313##                                                 145     COOCH(CH.sub.3).sub.2                                                                      ##STR314##                                                 146     COOCH(CH.sub.3).sub.2                                                                      ##STR315##                                                 147     COOCH(CH.sub.3).sub.2                                                                      ##STR316##                                            

    TABLE 19                                                                       __________________________________________________________________________     ArCHC(COOR).sub.2                  (3)                                         Compound No.                                                                            R     Ar                                                              __________________________________________________________________________     148      CH.sub.3                                                                              ##STR317##                                                     149      CH.sub.3                                                                              ##STR318##                                                     150      CH.sub.3                                                                              ##STR319##                                                     151      CH.sub.3                                                                              ##STR320##                                                     152      CH.sub.3                                                                              ##STR321##                                                     153      CH.sub.3                                                                              ##STR322##                                                     154      CH.sub.3                                                                              ##STR323##                                                     155      CH.sub.3                                                                              ##STR324##                                                     156      CH.sub.3                                                                              ##STR325##                                                     157      CH.sub.3                                                                              ##STR326##                                                     158      CH.sub.3                                                                              ##STR327##                                                     159      CH.sub.3                                                                              ##STR328##                                                     160      CH.sub.3                                                                              ##STR329##                                                     161      C.sub.4 H.sub.9                                                                       ##STR330##                                                     162      C.sub.4 H.sub.9                                                                       ##STR331##                                                     163      C.sub.4 H.sub.9                                                                       ##STR332##                                                     164      C.sub.4 H.sub.9                                                                       ##STR333##                                                     165      C.sub.4 H.sub.9                                                                       ##STR334##                                                     166      C.sub.4 H.sub.9                                                                       ##STR335##                                                     167      C.sub.4 H.sub.9                                                                       ##STR336##                                                     168      C.sub.4 H.sub.9                                                                       ##STR337##                                                     169      C.sub.4 H.sub.9                                                                       ##STR338##                                                     170      C.sub.4 H.sub.9                                                                       ##STR339##                                                     171      C.sub.4 H.sub.9                                                                       ##STR340##                                                     172      C.sub.4 H.sub.9                                                                       ##STR341##                                                     173                                                                                      ##STR342##                                                                           ##STR343##                                                     174                                                                                      ##STR344##                                                                           ##STR345##                                                     175                                                                                      ##STR346##                                                                           ##STR347##                                                     176                                                                                      ##STR348##                                                                           ##STR349##                                                     177                                                                                      ##STR350##                                                                           ##STR351##                                                     178                                                                                      ##STR352##                                                                           ##STR353##                                                     179                                                                                      ##STR354##                                                                           ##STR355##                                                     180                                                                                      ##STR356##                                                                           ##STR357##                                                     181                                                                                      ##STR358##                                                                           ##STR359##                                                     __________________________________________________________________________

                  TABLE 20                                                         ______________________________________                                          ##STR360##                    (4)                                             Compound No.                                                                              Formula                                                             ______________________________________                                          1                                                                                         ##STR361##                                                          2                                                                                         ##STR362##                                                          3                                                                                         ##STR363##                                                          4                                                                                         ##STR364##                                                          5                                                                                         ##STR365##                                                          6                                                                                         ##STR366##                                                          7                                                                                         ##STR367##                                                          8                                                                                         ##STR368##                                                          9                                                                                         ##STR369##                                                         10                                                                                         ##STR370##                                                         11                                                                                         ##STR371##                                                         12                                                                                         ##STR372##                                                         13                                                                                         ##STR373##                                                         14                                                                                         ##STR374##                                                         15                                                                                         ##STR375##                                                         16                                                                                         ##STR376##                                                         17                                                                                         ##STR377##                                                         18                                                                                         ##STR378##                                                         19                                                                                         ##STR379##                                                         20                                                                                         ##STR380##                                                         21                                                                                         ##STR381##                                                         22                                                                                         ##STR382##                                                         23                                                                                         ##STR383##                                                         24                                                                                         ##STR384##                                                         25                                                                                         ##STR385##                                                         26                                                                                         ##STR386##                                                         27                                                                                         ##STR387##                                                         28                                                                                         ##STR388##                                                         29                                                                                         ##STR389##                                                         30                                                                                         ##STR390##                                                         31                                                                                         ##STR391##                                                         32                                                                                         ##STR392##                                                         33                                                                                         ##STR393##                                                         34                                                                                         ##STR394##                                                         35                                                                                         ##STR395##                                                         36                                                                                         ##STR396##                                                         ______________________________________                                    

                  TABLE 21                                                         ______________________________________                                         ArCHCHNO.sub.2                 (5)                                             Compound No.                                                                               Ar                                                                 ______________________________________                                          1                                                                                          ##STR397##                                                         2                                                                                          ##STR398##                                                         3                                                                                          ##STR399##                                                         4                                                                                          ##STR400##                                                         5                                                                                          ##STR401##                                                         6                                                                                          ##STR402##                                                         7                                                                                          ##STR403##                                                         8                                                                                          ##STR404##                                                         9                                                                                          ##STR405##                                                        10                                                                                          ##STR406##                                                        11                                                                                          ##STR407##                                                        12                                                                                          ##STR408##                                                        13                                                                                          ##STR409##                                                        14                                                                                          ##STR410##                                                        15                                                                                          ##STR411##                                                        16                                                                                          ##STR412##                                                        17                                                                                          ##STR413##                                                        18                                                                                          ##STR414##                                                        19                                                                                          ##STR415##                                                        20                                                                                          ##STR416##                                                        21                                                                                          ##STR417##                                                        22                                                                                          ##STR418##                                                        23                                                                                          ##STR419##                                                        24                                                                                          ##STR420##                                                        25                                                                                          ##STR421##                                                        26                                                                                          ##STR422##                                                        27                                                                                          ##STR423##                                                        28                                                                                          ##STR424##                                                        29                                                                                          ##STR425##                                                        30                                                                                          ##STR426##                                                        31                                                                                          ##STR427##                                                        32                                                                                          ##STR428##                                                        33                                                                                          ##STR429##                                                        34                                                                                          ##STR430##                                                        ______________________________________                                    

                                      TABLE 22                                     __________________________________________________________________________      ##STR431##                        (6)                                         Compound No.  R.sup.1  R.sup.2                                                 __________________________________________________________________________      1                                                                                      ##STR432##                                                                                    ##STR433##                                              2                                                                                      ##STR434##                                                                                    ##STR435##                                              3                                                                                      ##STR436##                                                                                    ##STR437##                                              4                                                                                      ##STR438##                                                                                    ##STR439##                                              5                                                                                      ##STR440##                                                                                    ##STR441##                                              6                                                                                      ##STR442##                                                                                    ##STR443##                                              7                                                                                      ##STR444##                                                                                    ##STR445##                                              8                                                                                      ##STR446##                                                                                    ##STR447##                                              9                                                                                      ##STR448##                                                                                    ##STR449##                                             10                                                                                      ##STR450##                                                                                    ##STR451##                                             11                                                                                      ##STR452##                                                                                    ##STR453##                                             12                                                                                      ##STR454##                                                                                    ##STR455##                                             13                                                                                      ##STR456##                                                                                    ##STR457##                                             14                                                                                      ##STR458##                                                                                    ##STR459##                                             15                                                                                      ##STR460##                                                                                    ##STR461##                                             16                                                                                      ##STR462##                                                                                    ##STR463##                                             17                                                                                      ##STR464##                                                                                    ##STR465##                                             18                                                                                      ##STR466##                                                                                    ##STR467##                                             19                                                                                      ##STR468##                                                                                    ##STR469##                                             20                                                                                      ##STR470##                                                                                    ##STR471##                                             21                                                                                      ##STR472##                                                                                    ##STR473##                                             22                                                                                      ##STR474##                                                                                    ##STR475##                                             23                                                                                      ##STR476##                                                                                    ##STR477##                                             24                                                                                      ##STR478##                                                                                    ##STR479##                                             25                                                                                      ##STR480##                                                                                    ##STR481##                                             26                                                                                      ##STR482##                                                                                    ##STR483##                                             27                                                                                      ##STR484##                                                                                    ##STR485##                                             28                                                                                      ##STR486##                                                                                    ##STR487##                                             29                                                                                      ##STR488##                                                                                    ##STR489##                                             30                                                                                      ##STR490##                                                                                    ##STR491##                                             31                                                                                      ##STR492##                                                                                    ##STR493##                                             32                                                                                      ##STR494##                                                                                    ##STR495##                                             33                                                                                      ##STR496##                                                                                    ##STR497##                                             34                                                                                      ##STR498##                                                                                    ##STR499##                                             35                                                                                      ##STR500##                                                                                    ##STR501##                                             36                                                                                      ##STR502##                                                                                    ##STR503##                                             37                                                                                      ##STR504##                                                                                    ##STR505##                                             38                                                                                      ##STR506##                                                                                    ##STR507##                                             39                                                                                      ##STR508##                                                                                    ##STR509##                                             40                                                                                      ##STR510##                                                                                    ##STR511##                                             41                                                                                      ##STR512##                                                                                    ##STR513##                                             42                                                                                      ##STR514##                                                                                    ##STR515##                                             43                                                                                      ##STR516##                                                                                    ##STR517##                                             44                                                                                      ##STR518##                                                                                    ##STR519##                                             45                                                                                      ##STR520##                                                                                    ##STR521##                                             46                                                                                      ##STR522##                                                                                    ##STR523##                                             47                                                                                      ##STR524##                                                                                    ##STR525##                                             48                                                                                      ##STR526##                                                                                    ##STR527##                                             49                                                                                      ##STR528##                                                                                    ##STR529##                                             50                                                                                      ##STR530##                                                                                    ##STR531##                                             51                                                                                      ##STR532##                                                                                    ##STR533##                                             52                                                                                      ##STR534##                                                                                    ##STR535##                                             53                                                                                      ##STR536##                                                                                    ##STR537##                                             54                                                                                      ##STR538##                                                                                    ##STR539##                                             55                                                                                      ##STR540##                                                                                    ##STR541##                                             56                                                                                      ##STR542##                                                                                    ##STR543##                                             57                                                                                      ##STR544##                                                                                    ##STR545##                                             58                                                                                      ##STR546##                                                                                    ##STR547##                                             59                                                                                      ##STR548##                                                                                    ##STR549##                                             60                                                                                      ##STR550##                                                                                    ##STR551##                                             61                                                                                      ##STR552##                                                                                    ##STR553##                                             62                                                                                      ##STR554##                                                                                    ##STR555##                                             63                                                                                      ##STR556##                                                                                    ##STR557##                                             64                                                                                      ##STR558##                                                                                    ##STR559##                                             65                                                                                      ##STR560##                                                                                    ##STR561##                                             66                                                                                      ##STR562##                                                                                    ##STR563##                                             __________________________________________________________________________

                  TABLE 23                                                         ______________________________________                                          ##STR564##                    (7)                                             Compound                                                                       No.     R.sup.1          R.sup.2                                               ______________________________________                                          1      H                4'-NO.sub.2                                            2      H                3'-NO.sub.2                                            3      H                3'-COOC.sub.2 H.sub.5 -4'-NO.sub.2                     4      H                3'-NO.sub.2 -4'-F                                      5      H                3'-NO.sub.2 -4'-Cl                                     6      H                3'-NO.sub.2 -4'-CH.sub.3                               7      H                4'-CN                                                  8      H                3'-CN                                                  9      H                3'-CF.sub.3 -4'-CN                                    10      H                4'-Cl                                                 11      H                3'-Cl                                                 12      H                4'-Br                                                 13      H                3'-Br                                                 14      H                3'-Cl-4'-CH.sub.3                                     15      H                3'-CF.sub.3 -4'-F                                     16      H                3'-CF.sub.3 -4'-Cl                                    17      H                3'-Cl-4'-F                                            18      H                3',4'-diF                                             19      H                3',4'-diCl                                            20      H                3',5'-diCl                                            21      H                2',4',5'-triCl                                        22      H                4'-COOC.sub.2 H.sub.5                                 23      H                4'-COOC.sub.4 H.sub.9                                 24      H                4'-CONHC.sub.4 H.sub.9                                25      H                4'-CON(C.sub.4 H.sub.9).sub.2                         26      H                3'-CF.sub.3                                           27      H                4'-CF.sub.3                                           28      H                4'-CH.sub.3                                           29      H                4'-C.sub.2 H.sub.5                                    30      H                4'-C.sub.4 H.sub.9                                    31      H                4'-C.sub.6 H.sub.13                                   32      H                                                                                                ##STR565##                                           33      H                3',4'-diCH.sub.3                                      34      H                H                                                     35      Cl               4'-NO.sub.2                                           36      Cl               3'-NO.sub.2                                           37      Cl               3'-NO.sub.2 -4'-CH.sub.3                              38      Cl               4'-CN                                                 39      Cl               4'-Cl                                                 40      Cl               3'-CF.sub.3 -4'-F                                     41      Cl               3',4'-diCl                                            42      Cl               4'-COOC.sub.2 H.sub.5                                 43      Cl               4'-CF.sub.3                                           44      Cl               4'-C.sub.4 H.sub.9                                    45      Br               4'-NO.sub.2                                           46      Br               4'-CN                                                 47      Br               4'-COOC.sub.2 H.sub.5                                 48      Br               4'-CF.sub.3                                           49                                                                                      ##STR566##      4'-NO.sub.2                                           50                                                                                      ##STR567##      3'-NO.sub.2                                           51                                                                                      ##STR568##      3'-NO.sub.2 -4'-CH.sub.3                              52                                                                                      ##STR569##      4'-CN                                                 53                                                                                      ##STR570##      4'-Cl                                                 54                                                                                      ##STR571##      3',4'-diCl                                            55                                                                                      ##STR572##      4'-COOC.sub.2 H.sub.5                                 56                                                                                      ##STR573##      4'-COOC.sub.4 H.sub.9                                 57                                                                                      ##STR574##      4'-COON(C.sub.4 H.sub.9).sub.2                        58                                                                                      ##STR575##      4'-CF.sub.3                                           59                                                                                      ##STR576##      4'-C.sub.2 H.sub.5                                    60                                                                                      ##STR577##      4'-C.sub.4 H.sub.9                                    61                                                                                      ##STR578##      H                                                     62                                                                                      ##STR579##      4'-NO.sub.2                                           63                                                                                      ##STR580##      4'-COOC.sub.2 H.sub.5                                 64                                                                                      ##STR581##      4'-COOC.sub.4 H.sub.9                                 65                                                                                      ##STR582##      4'-Cl                                                 66                                                                                      ##STR583##      4'-CF.sub.3                                           67                                                                                      ##STR584##      4'-C.sub.4 H.sub.9                                    68      CH.sub.3         4'-NO.sub.2                                           69      CH.sub.3         4'-CN                                                 70      CH.sub.3         4'-Cl                                                 71      CH.sub.3         4'-COOC.sub.2 H.sub.5                                 72      CH.sub.3         4'-COOC.sub.4 H.sub.9                                 73      CH.sub.3         4'-CF.sub.3                                           74      CH.sub.3         4'-C.sub.2 H.sub.5                                    75      CH.sub.3         4'-C.sub.4 H.sub.9                                    ______________________________________                                    

                  TABLE 24                                                         ______________________________________                                          ##STR585##                    (8)                                             Compound No.         R.sup.3                                                   ______________________________________                                         76                   4'-NO.sub.2                                               77                   3'-NO.sub.2                                               78                   4'-CN                                                     79                   4'-Cl                                                     80                   3'-Cl                                                     81                   4'-COOC.sub.2 H.sub.5                                     82                   4'-COOC.sub.4 H.sub.9                                     83                   4'-CF.sub.3                                               84                   4'-C.sub.2 H.sub.5                                        85                   4'-C.sub.4 H.sub.9                                        86                   4'-C.sub.6 H.sub.13                                       87                   H                                                         ______________________________________                                    

                  TABLE 25                                                         ______________________________________                                          ##STR586##                    (9)                                             Com-                                                                           pound                                                                          No.    R.sup.1        R.sup.2                                                  ______________________________________                                          1                                                                                     ##STR587##                                                                                    ##STR588##                                               2                                                                                     ##STR589##                                                                                    ##STR590##                                               3                                                                                     ##STR591##                                                                                    ##STR592##                                               4                                                                                     ##STR593##                                                                                    ##STR594##                                               5                                                                                     ##STR595##                                                                                    ##STR596##                                               6                                                                                     ##STR597##                                                                                    ##STR598##                                               7                                                                                     ##STR599##                                                                                    ##STR600##                                               8                                                                                     ##STR601##                                                                                    ##STR602##                                               9                                                                                     ##STR603##                                                                                    ##STR604##                                              10                                                                                     ##STR605##                                                                                    ##STR606##                                              11                                                                                     ##STR607##                                                                                    ##STR608##                                              12                                                                                     ##STR609##                                                                                    ##STR610##                                              13                                                                                     ##STR611##                                                                                    ##STR612##                                              14                                                                                     ##STR613##                                                                                    ##STR614##                                              15                                                                                     ##STR615##                                                                                    ##STR616##                                              16                                                                                     ##STR617##                                                                                    ##STR618##                                              17                                                                                     ##STR619##                                                                                    ##STR620##                                              18                                                                                     ##STR621##                                                                                    ##STR622##                                              19                                                                                     ##STR623##                                                                                    ##STR624##                                              20                                                                                     ##STR625##                                                                                    ##STR626##                                              21                                                                                     ##STR627##                                                                                    ##STR628##                                              22                                                                                     ##STR629##                                                                                    ##STR630##                                              23                                                                                     ##STR631##                                                                                    ##STR632##                                              24                                                                                     ##STR633##                                                                                    ##STR634##                                              25                                                                                     ##STR635##                                                                                    ##STR636##                                              26                                                                                     ##STR637##                                                                                    ##STR638##                                              27                                                                                     ##STR639##                                                                                    ##STR640##                                              28                                                                                     ##STR641##                                                                                    ##STR642##                                              29                                                                                     ##STR643##                                                                                    ##STR644##                                              30                                                                                     ##STR645##                                                                                    ##STR646##                                              31                                                                                     ##STR647##                                                                                    ##STR648##                                              32                                                                                     ##STR649##                                                                                    ##STR650##                                              33                                                                                     ##STR651##                                                                                    ##STR652##                                              34                                                                                     ##STR653##                                                                                    ##STR654##                                              35                                                                                     ##STR655##                                                                                    ##STR656##                                              36                                                                                     ##STR657##                                                                                    ##STR658##                                              37                                                                                     ##STR659##                                                                                    ##STR660##                                              38                                                                                     ##STR661##                                                                                    ##STR662##                                              39                                                                                     ##STR663##                                                                                    ##STR664##                                              40                                                                                     ##STR665##                                                                                    ##STR666##                                              41                                                                                     ##STR667##                                                                                    ##STR668##                                              42                                                                                     ##STR669##                                                                                    ##STR670##                                              43                                                                                     ##STR671##                                                                                    ##STR672##                                              44                                                                                     ##STR673##                                                                                    ##STR674##                                              45                                                                                     ##STR675##                                                                                    ##STR676##                                              46                                                                                     ##STR677##                                                                                    ##STR678##                                              47                                                                                     ##STR679##                                                                                    ##STR680##                                              48                                                                                     ##STR681##                                                                                    ##STR682##                                              49                                                                                     ##STR683##                                                                                    ##STR684##                                              50                                                                                     ##STR685##                                                                                    ##STR686##                                              51                                                                                     ##STR687##                                                                                    ##STR688##                                              52                                                                                     ##STR689##                                                                                    ##STR690##                                              53                                                                                     ##STR691##                                                                                    ##STR692##                                              54                                                                                     ##STR693##                                                                                    ##STR694##                                              55                                                                                     ##STR695##                                                                                    ##STR696##                                              56                                                                                     ##STR697##                                                                                    ##STR698##                                              57                                                                                     ##STR699##                                                                                    ##STR700##                                              58                                                                                     ##STR701##                                                                                    ##STR702##                                              59                                                                                     ##STR703##                                                                                    ##STR704##                                              60                                                                                     ##STR705##                                                                                    ##STR706##                                              61                                                                                     ##STR707##                                                                                    ##STR708##                                              62                                                                                     ##STR709##                                                                                    ##STR710##                                              63                                                                                     ##STR711##                                                                                    ##STR712##                                              64                                                                                     ##STR713##                                                                                    ##STR714##                                              65                                                                                     ##STR715##                                                                                    ##STR716##                                              66                                                                                     ##STR717##                                                                                    ##STR718##                                              67                                                                                     ##STR719##                                                                                    ##STR720##                                              68                                                                                     ##STR721##                                                                                    ##STR722##                                              69                                                                                     ##STR723##                                                                                    ##STR724##                                              70                                                                                     ##STR725##                                                                                    ##STR726##                                              71                                                                                     ##STR727##                                                                                    ##STR728##                                              72                                                                                     ##STR729##                                                                                    ##STR730##                                              73                                                                                     ##STR731##                                                                                    ##STR732##                                              74                                                                                     ##STR733##                                                                                    ##STR734##                                              75                                                                                     ##STR735##                                                                                    ##STR736##                                              76                                                                                     ##STR737##                                                                                    ##STR738##                                              77                                                                                     ##STR739##                                                                                    ##STR740##                                              78                                                                                     ##STR741##                                                                                    ##STR742##                                              79                                                                                     ##STR743##                                                                                    ##STR744##                                              80                                                                                     ##STR745##                                                                                    ##STR746##                                              81                                                                                     ##STR747##                                                                                    ##STR748##                                              82                                                                                     ##STR749##                                                                                    ##STR750##                                              83                                                                                     ##STR751##                                                                                    ##STR752##                                              84                                                                                     ##STR753##                                                                                    ##STR754##                                              85                                                                                     ##STR755##                                                                                    ##STR756##                                              86                                                                                     ##STR757##                                                                                    ##STR758##                                              87                                                                                     ##STR759##                                                                                    ##STR760##                                              88                                                                                     ##STR761##                                                                                    ##STR762##                                              89                                                                                     ##STR763##                                                                                    ##STR764##                                              90                                                                                     ##STR765##                                                                                    ##STR766##                                              91                                                                                     ##STR767##                                                                                    ##STR768##                                              92                                                                                     ##STR769##                                                                                    ##STR770##                                              93                                                                                     ##STR771##                                                                                    ##STR772##                                              94                                                                                     ##STR773##                                                                                    ##STR774##                                              95                                                                                     ##STR775##                                                                                    ##STR776##                                              96                                                                                     ##STR777##                                                                                    ##STR778##                                              97                                                                                     ##STR779##                                                                                    ##STR780##                                              98                                                                                     ##STR781##                                                                                    ##STR782##                                              99                                                                                     ##STR783##                                                                                    ##STR784##                                              100                                                                                    ##STR785##                                                                                    ##STR786##                                              101                                                                                    ##STR787##                                                                                    ##STR788##                                              102                                                                                    ##STR789##                                                                                    ##STR790##                                              103                                                                                    ##STR791##                                                                                    ##STR792##                                              104                                                                                    ##STR793##                                                                                    ##STR794##                                              105                                                                                    ##STR795##                                                                                    ##STR796##                                              106                                                                                    ##STR797##                                                                                    ##STR798##                                              107                                                                                    ##STR799##                                                                                    ##STR800##                                              108                                                                                    ##STR801##                                                                                    ##STR802##                                              109                                                                                    ##STR803##                                                                                    ##STR804##                                              110                                                                                    ##STR805##                                                                                    ##STR806##                                              111                                                                                    ##STR807##                                                                                    ##STR808##                                              112                                                                                    ##STR809##                                                                                    ##STR810##                                              113                                                                                    ##STR811##                                                                                    ##STR812##                                              114                                                                                    ##STR813##                                                                                    ##STR814##                                              115                                                                                    ##STR815##                                                                                    ##STR816##                                              116                                                                                    ##STR817##                                                                                    ##STR818##                                              117                                                                                    ##STR819##                                                                                    ##STR820##                                              118                                                                                    ##STR821##                                                                                    ##STR822##                                              119                                                                                    ##STR823##                                                                                    ##STR824##                                              120                                                                                    ##STR825##                                                                                    ##STR826##                                              121                                                                                    ##STR827##                                                                                    ##STR828##                                              122                                                                                    ##STR829##                                                                                    ##STR830##                                              123                                                                                    ##STR831##                                                                                    ##STR832##                                              124                                                                                    ##STR833##                                                                                    ##STR834##                                              125                                                                                    ##STR835##                                                                                    ##STR836##                                              126                                                                                    ##STR837##                                                                                    ##STR838##                                              127                                                                                    ##STR839##                                                                                    ##STR840##                                              128                                                                                    ##STR841##                                                                                    ##STR842##                                              129                                                                                    ##STR843##                                                                                    ##STR844##                                              130                                                                                    ##STR845##                                                                                    ##STR846##                                              131                                                                                    ##STR847##                                                                                    ##STR848##                                              132                                                                                    ##STR849##                                                                                    ##STR850##                                              133                                                                                    ##STR851##                                                                                    ##STR852##                                              134                                                                                    ##STR853##                                                                                    ##STR854##                                              135                                                                                    ##STR855##                                                                                    ##STR856##                                              136                                                                                    ##STR857##                                                                                    ##STR858##                                              137                                                                                    ##STR859##                                                                                    ##STR860##                                              138                                                                                    ##STR861##                                                                                    ##STR862##                                              139                                                                                    ##STR863##                                                                                    ##STR864##                                              140                                                                                    ##STR865##                                                                                    ##STR866##                                              141                                                                                    ##STR867##                                                                                    ##STR868##                                              142                                                                                    ##STR869##                                                                                    ##STR870##                                              143                                                                                    ##STR871##                                                                                    ##STR872##                                              144                                                                                    ##STR873##                                                                                    ##STR874##                                              145                                                                                    ##STR875##                                                                                    ##STR876##                                              146                                                                                    ##STR877##                                                                                    ##STR878##                                              147                                                                                    ##STR879##                                                                                    ##STR880##                                              148                                                                                    ##STR881##                                                                                    ##STR882##                                              149                                                                                    ##STR883##                                                                                    ##STR884##                                              150                                                                                    ##STR885##                                                                                    ##STR886##                                              151                                                                                    ##STR887##                                                                                    ##STR888##                                              152                                                                                    ##STR889##                                                                                    ##STR890##                                              153                                                                                    ##STR891##                                                                                    ##STR892##                                              154                                                                                    ##STR893##                                                                                    ##STR894##                                              155                                                                                    ##STR895##                                                                                    ##STR896##                                              156                                                                                    ##STR897##                                                                                    ##STR898##                                              157                                                                                    ##STR899##                                                                                    ##STR900##                                              158                                                                                    ##STR901##                                                                                    ##STR902##                                              159                                                                                    ##STR903##                                                                                    ##STR904##                                              160                                                                                    ##STR905##                                                                                    ##STR906##                                              161                                                                                    ##STR907##                                                                                    ##STR908##                                              162                                                                                    ##STR909##                                                                                    ##STR910##                                              163                                                                                    ##STR911##                                                                                    ##STR912##                                              164                                                                                    ##STR913##                                                                                    ##STR914##                                              165                                                                                    ##STR915##                                                                                    ##STR916##                                              166                                                                                    ##STR917##                                                                                    ##STR918##                                              167                                                                                    ##STR919##                                                                                    ##STR920##                                              168                                                                                    ##STR921##                                                                                    ##STR922##                                              169                                                                                    ##STR923##                                                                                    ##STR924##                                              170                                                                                    ##STR925##                                                                                    ##STR926##                                              171                                                                                    ##STR927##                                                                                    ##STR928##                                              172                                                                                    ##STR929##                                                                                    ##STR930##                                              173                                                                                    ##STR931##                                                                                    ##STR932##                                              174                                                                                    ##STR933##                                                                                    ##STR934##                                              175                                                                                    ##STR935##                                                                                    ##STR936##                                              176                                                                                    ##STR937##                                                                                    ##STR938##                                              ______________________________________                                    

                                      TABLE 26                                     __________________________________________________________________________      ##STR939##                                                                    Compound                                                                       No.   R.sup.1                R.sup.2                                           __________________________________________________________________________      1    4-COOCH.sub.3          H                                                  2    4-COOCH.sub.3          7-NO.sub.2                                         3    2-C(CH.sub.3).sub.3 -4-NO.sub.2                                                                       5-NO.sub.2 -7-NO.sub.2                             4    4-COOC.sub.2 H.sub.5   H                                                  5    2-COOC.sub.4 H.sub.9   H                                                  6    4-COOC.sub.4 H.sub.9   H                                                  7    4-COOC.sub.8 H.sub.17  H                                                  8    2-C(CH.sub.3).sub.3 -4-COOC.sub.4 H.sub.9                                                             7-C(CH.sub.3).sub.3                                9                                                                                    ##STR940##            H                                                 10                                                                                    ##STR941##            H                                                 11    2,4-di-NO.sub.2        7-NO.sub.2                                        12                                                                                    ##STR942##            H                                                 13                                                                                    ##STR943##            H                                                 14                                                                                    ##STR944##            H                                                 15    2-CH.sub.3             7-CH.sub.3                                        __________________________________________________________________________

                  TABLE 27                                                         ______________________________________                                          ##STR945##                                                                    Compound                                                                       No.      R.sup.3      R.sup.4                                                  ______________________________________                                          1       H            H                                                         2       4-NO.sub.2   H                                                         3       3-NO.sub.2   H                                                         4       4-NO.sub.2   4'-CH.sub.3                                               5       H            2'-CH.sub.3                                               6       4-NO.sub.2   4'-OCH.sub.3                                              7       4-NO.sub.2                                                                                   ##STR946##                                               8       4-NO.sub.2                                                                                   ##STR947##                                               9       4-CH.sub.3   4'-CH.sub.3                                              10       2,4-di-NO.sub.2                                                                             H                                                        11       H                                                                                            ##STR948##                                              12       4-Cl         4'-Cl                                                    13       H            3'-COOC.sub.4 H.sub.9                                    14       3-NO.sub.2   4'-COOC.sub.4 H.sub.9                                    15       4-NO.sub.2                                                                                   ##STR949##                                              16       4-NO.sub.2   4'-I                                                     17       4-CN         4'-NO.sub.2                                              18       4-CN         4'-COOC.sub.4 H.sub.9                                    19       4,5-di-COOC.sub.2 H.sub.5                                                                   3',4'-di-COOC.sub.2 H.sub.5                              20       3-NO.sub.2 -4-C.sub.4 H.sub.9                                                               3'-NO.sub.2 -4'-C.sub.4 H.sub.9                          21       4-NO.sub.2                                                                                   ##STR950##                                              22       H                                                                                            ##STR951##                                              23       4-NO.sub.2   H                                                        ______________________________________                                    

                                      TABLE 28                                     __________________________________________________________________________      ##STR952##                                                                    Compound                                                                       No.   R.sup.5                R.sup.6                                           __________________________________________________________________________      1    4-COOCH.sub.3          H                                                  2    4-COOCH.sub.3          7-NO.sub.2                                         3    2-C(CH.sub.3).sub.3 -4-NO.sub.2                                                                       5-NO.sub.2 -7-NO.sub.2                             4    4-COOC.sub.2 H.sub.5   H                                                  5    2-COOC.sub.4 H.sub.9   H                                                  6    4-COOC.sub.4 H.sub.9   H                                                  7    4-COOC.sub.8 H.sub.17  H                                                  8    2-C(CH.sub.3).sub.3 -4-COOC.sub.4 H.sub.9                                                             7-C(CH.sub.3).sub.3                                9                                                                                    ##STR953##            H                                                 10                                                                                    ##STR954##            H                                                 11    2,4-di-NO.sub.2        7-NO.sub.2                                        12                                                                                    ##STR955##            H                                                 13                                                                                    ##STR956##            H                                                 14                                                                                    ##STR957##            H                                                 15    2-CH.sub.3             7-CH.sub.3                                        __________________________________________________________________________

                  TABLE 29                                                         ______________________________________                                          ##STR958##                                                                    Compound                                                                       No.      R.sup.7      R.sup.8                                                  ______________________________________                                          1       H            H                                                         2       4-NO.sub.2   H                                                         3       3-NO.sub.2   H                                                         4       4-NO.sub.2   4'-CH.sub.3                                               5       H            2'-CH.sub.3                                               6       4-NO.sub.2   4'-OCH.sub.3                                              7       4-NO.sub.2                                                                                   ##STR959##                                               8       4-NO.sub.2                                                                                   ##STR960##                                               9       4-CH.sub.3   4'-CH.sub.3                                              10       2,4-di-NO.sub.2                                                                             H                                                        11       H                                                                                            ##STR961##                                              12       4-Cl         4'-Cl                                                    13       H            3'-COOC.sub.4 H.sub.9                                    14       3-NO.sub.2   4'-COOC.sub.4 H.sub.9                                    15       4-NO.sub.2                                                                                   ##STR962##                                              16       4-NO.sub.2   4'-I                                                     17       4-CN         4'-NO.sub.2                                              18       4-CN         4'-COOC.sub.4 H.sub.9                                    19       4,5-di-COOC.sub.2 H.sub.5                                                                   3',4'-di-COOC.sub.2 H.sub.5                              20       3-NO.sub.2 -4-C.sub.4 H.sub.9                                                               3'-NO.sub.2 -4'-C.sub.4 H.sub.9                          21       4-NO.sub.2                                                                                   ##STR963##                                              22       H                                                                                            ##STR964##                                              23       4-NO.sub.2   H                                                        ______________________________________                                    

                  TABLE 30                                                         ______________________________________                                          ##STR965##                                                                    Compound                                                                       No.       R                                                                    ______________________________________                                          1                                                                                        ##STR966##                                                           2                                                                                        ##STR967##                                                           3                                                                                        ##STR968##                                                           4                                                                                        ##STR969##                                                           5                                                                                        ##STR970##                                                           6                                                                                        ##STR971##                                                           7                                                                                        ##STR972##                                                           8                                                                                        ##STR973##                                                           9                                                                                        ##STR974##                                                          10                                                                                        ##STR975##                                                          11                                                                                        ##STR976##                                                          12                                                                                        ##STR977##                                                          13                                                                                        ##STR978##                                                          14                                                                                        ##STR979##                                                          15                                                                                        ##STR980##                                                          16                                                                                        ##STR981##                                                          17                                                                                        ##STR982##                                                          18                                                                                        ##STR983##                                                          19                                                                                        ##STR984##                                                          20                                                                                        ##STR985##                                                          21                                                                                        ##STR986##                                                          22                                                                                        ##STR987##                                                          23                                                                                        ##STR988##                                                          24                                                                                        ##STR989##                                                          25                                                                                        ##STR990##                                                          26                                                                                        ##STR991##                                                          27                                                                                        ##STR992##                                                          28                                                                                        ##STR993##                                                          29                                                                                        ##STR994##                                                          30                                                                                        ##STR995##                                                          31                                                                                        ##STR996##                                                          32                                                                                        ##STR997##                                                          33                                                                                        ##STR998##                                                          34                                                                                        ##STR999##                                                          35                                                                                        ##STR1000##                                                         36                                                                                        ##STR1001##                                                         37                                                                                        ##STR1002##                                                         38                                                                                        ##STR1003##                                                         39                                                                                        ##STR1004##                                                         40                                                                                        ##STR1005##                                                         41                                                                                        ##STR1006##                                                         42                                                                                        ##STR1007##                                                         43                                                                                        ##STR1008##                                                         44                                                                                        ##STR1009##                                                         45                                                                                        ##STR1010##                                                         46                                                                                        ##STR1011##                                                         ______________________________________                                    

Furthermore, when at least one organic acceptor compound of formula (A), (B) or (C) is employed in the single-layered photoconductive layer, not only the sensitizing effect is improved, but also the decrease of the charging characteristics can be prevented during the repeated operations and the charging stability is remarkably improved.

[Organic Acceptor Compound of Formula (A)] ##STR1012## wherein R¹, R², and R³ each is hydrogen, a substituted or unsubstituted alkyl group, an alkoxyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted sulfonamide group, a substituted or unsubstituted carbamoyl group, a halogen atom, cyano group, or nitro group, and R¹ may form a ring in combination with other atoms; k, l and m each is an integer of 1 to 4; and X is oxygen, sulfur or selenium.

[Organic Acceptor Compound of Formula (B)] ##STR1013## wherein R¹, R², R³ and R⁴ may be the same or different, and each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, cyano group, or nitro group; and X is ##STR1014## in which R⁵ and R⁶ may be the same or different and each is hydrogen, a halogen atom, cyano group, a substituted or unsubstituted aromatic group, or --COOR⁷ in which R⁷ is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic group; or

N--R⁸, in which R⁸ is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, or cyano group.

[Organic Acceptor Compound of Formula (C)] ##STR1015## wherein R¹ may be the same or different, and is a halogen atom, nitro group, or a substituted or unsubstituted alkyl group; X is ═O, N--R²,

in which R² is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group, or ##STR1016## in which R³ and R⁴ may be the same or different and each is hydrogen, cyano group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted phenoxycarbonyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group; and

p is an integer of 0 to 4, provided that when X is oxygen, p is an integer of 1 to 4.

TABLES 31-32 show specific examples of the organic acceptor compound of formulae (A) and (B), and TABLES 33-35 show specific examples of the organic acceptor compounds of formula (C).

                  TABLE 31                                                         ______________________________________                                          ##STR1017##                                                                   Compound                                                                       No.     k     l     m   X.sup.3                                                                            R.sup.14                                                                               R.sup.15                                                                             R.sup.16                             ______________________________________                                         A-1     0     0     1   S   H       H     2-COOC.sub.4 H.sub.9                 A-2     0     0     1   S   H       H     4-COOC.sub.4 H.sub.9                 A-3     0     0     1   S   H       H     1-COOC.sub.4 H.sub.9                 A-4     0     0     1   S   H       H     3-COOC.sub.4 H.sub.9                 A-5     0     0     1   S   H       H     1-COOCH.sub.3                        A-6     0     0     1   S   H       H     2-COOC.sub.5 H.sub.11                A-7     0     0     1   S   H       H     3-COOC.sub.5 H.sub.11                A-8     0     0     1   S   H       H     4-COOC.sub.5 H.sub.11                A-9     0     0     1   S   H       H     1-COOC.sub.6 H.sub.13                A-10    0     0     1   S   H       H     2-COOC.sub.6 H.sub.13                A-11    0     0     1   S   H       H     3-COOC.sub.6 H.sub.13                A-12    0     0     1   S   H       H     4-COOC.sub.6 H.sub.13                A-13    0     0     1   S   H       H     1-COOC.sub.7 H.sub.15                A-14    0     0     1   S   H       H     2-COOC.sub.7 H.sub.15                A-15    0     0     1   S   H       H     3-COOC.sub.7 H.sub.15                A-16    0     0     1   S   H       H     4-COOC.sub.7 H.sub.15                A-17    0     0     1   S   H       H     1-COOC.sub.8 H.sub.17                A-18    0     0     1   S   H       H     2-COOC.sub.8 H.sub.17                A-19    0     0     1   S   H       H     3-COOC.sub.8 H.sub.17                A-20    0     0     1   S   H       H     4-COOC.sub.8 H.sub.17                A-21    0     0     1   O   H       H     2-COOC.sub.4 H.sub.9                 A-22    0     0     1   O   H       H     4-COOC.sub.4 H.sub.9                 A-23    0     0     1   O   H       H     1-COOC.sub.4 H.sub.9                 A-24    0     0     1   O   H       H     3-COOC.sub.4 H.sub.9                 A-25    0     0     1   O   H       H     1-COOCH.sub.3                        A-26    0     0     1   O   H       H     2-COOCH.sub.3                        A-27    0     0     1   O   H       H     3-COOCH.sub.3                        A-28    0     0     1   O   H       H     4-COOCH.sub.3                        A-29    0     0     1   O   H       H     1-COOC.sub.2 H.sub.5                 A-30    1     0     1   O   2-NO.sub.2                                                                             H     2-COOC.sub.7 H.sub.15                A-31    1     0     1   O   2-NO.sub.2                                                                             H     3-COOC.sub.7 H.sub.15                A-32    1     0     1   O   2-NO.sub.2                                                                             H     4-COOC.sub.7 H.sub.15                A-33    1     0     1   O   2-NO.sub.2                                                                             H     1-COOC.sub.8 H.sub.17                A-34    1     0     1   O   2-NO.sub.2                                                                             H     2-COOC.sub.8 H.sub.17                A-35    1     0     1   O   2-NO.sub.2                                                                             H     3-COOC.sub.8 H.sub.17                A-36    1     0     1   O   2-NO.sub.2                                                                             H     4-COOC.sub.8 H.sub.17                A-37    1     0     1   O   3-C(CH.sub.3).sub.3                                                                    H     2-COOC.sub.4 H.sub.9                 A-38    1     0     1   O   3-C(CH.sub.3).sub.3                                                                    H     4-COOC.sub.4 H.sub.9                 A-39    1     0     1   O   3-C(CH.sub.3).sub.3                                                                    H     1-COOC.sub.4 H.sub.9                 A-40    1     0     1   O   3-C(CH.sub.3).sub.3                                                                    H     3-COOC.sub.4 H.sub.9                 A-41    1     0     1   O   3-C(CH.sub.3).sub.3                                                                    H     1-COOCH.sub.3                        A-42    0     1     1   S   H       6-CF.sub.3                                                                           3-CF.sub.3                           A-43    0     1     2   S   H       7-CF.sub.3                                                                           2-CF.sub.3                                                                     4-C.sub.4 H.sub.9                    A-44    0     1     2   S   H       7-CF.sub.3                                                                           2-NO.sub.2                                                                     4-C.sub.8 H.sub.17                   A-45    0     1     2   S   H       7-NO.sub.2                                                                           2-NO.sub.2                                                                     4-NO.sub.2                           A-46    0     2     2   S   H       7-NO.sub.2                                                                           2-NO.sub.2                                                               5-NO.sub.2                                                                           4-NO.sub.2                           A-47    0     0     1   S   H       H     2-NO.sub.2                           A-48    0     1     1   S   H       7-NO.sub.2                                                                           2-NO.sub.2                           A-49    0     1     1   O   H       7-CN  4-COC.sub.8 H.sub.17                 A-50    0     1     1   O   H       7-CN  4-COOC.sub.4 H.sub.9                 A-51    0     1     1   O   H       7-CN  4-OC.sub.4 H.sub.9                   ______________________________________                                    

                                      TABLE 32                                     __________________________________________________________________________      ##STR1018##                                                                   Compound No.                                                                           X.sup.4      R.sup.17                                                                           R.sup.18                                                                           R.sup.19                                                                           R.sup.20                                      __________________________________________________________________________     B-1     O            H   H   H   H                                             B-2                                                                                     ##STR1019## H   H   H   H                                             B-3                                                                                     ##STR1020## H   H   H   H                                             B-4                                                                                     ##STR1021## H   H   H   H                                             B-5                                                                                     ##STR1022## H   H   H   H                                             B-6                                                                                     ##STR1023## H   H   H   H                                             B-7                                                                                     ##STR1024## H   H   H   H                                             B-8                                                                                     ##STR1025## H   H   H   H                                             B-9                                                                                     ##STR1026## H   H   H   H                                             B-10                                                                                    ##STR1027## H   H   H   H                                             B-11                                                                                    ##STR1028## H   H   H   H                                             B-12                                                                                    ##STR1029## H   H   H   H                                             B-13                                                                                    ##STR1030## H   H   H   H                                             B-14                                                                                    ##STR1031## H   H   H   H                                             B-15                                                                                    ##STR1032## H   H   H   H                                             B-16                                                                                    ##STR1033## H   H   H   H                                             B-17                                                                                    ##STR1034## H   H   H   H                                             B-18                                                                                    ##STR1035## H   H   H   H                                             B-19                                                                                    ##STR1036## H   H   H   H                                             B-20                                                                                    ##STR1037## H   H   H   H                                             B-21                                                                                    ##STR1038## H   H   H   H                                             B-22                                                                                    ##STR1039## H   H   H   H                                             B-23                                                                                    ##STR1040## H   H   H   H                                             B-24                                                                                    ##STR1041## H   H   H   H                                             B-25                                                                                    ##STR1042## H   H   H   H                                             B-26                                                                                    ##STR1043## H   H   H   H                                             B-27    O            4-CH.sub.3                                                                         H   2-CH.sub.3                                                                         H                                             B-28                                                                                    ##STR1044## 4-CH.sub.3                                                                         H   2-CH.sub.3                                                                         H                                             B-29                                                                                    ##STR1045## 4-CH.sub.3                                                                         H   2-CH.sub.3                                                                         H                                             B-30    O            4-CH.sub.3                                                                         4-CH.sub.3                                                                         2-CH.sub.3                                                                         H                                             B-31                                                                                    ##STR1046## 4-CH.sub.3                                                                         4-CH.sub.3                                                                         2-CH.sub.3                                                                         H                                             B-32                                                                                    ##STR1047## 4-CH.sub.3                                                                         4-CH.sub.3                                                                         2-CH.sub.3                                                                         H                                             B-33                                                                                    ##STR1048## 4-C.sub.4 H.sub.9                                                                  H   2-CH.sub.3                                                                         H                                             B-34                                                                                    ##STR1049## 3-CH.sub.3                                                                         H   3-C.sub.4 H.sub.9                                                                  H                                             B-35                                                                                    ##STR1050## 4-CF.sub.3                                                                         H   H   H                                             B-36                                                                                    ##STR1051## 4-Br                                                                               H   3-Br                                                                               4-Br                                          B-37                                                                                    ##STR1052## 4-NO.sub.2                                                                         H   H   H                                             B-38                                                                                    ##STR1053## 4-CN                                                                               H   H   H                                             B-39    O            H   H   2-NO.sub.2                                                                         H                                             B-40                                                                                    ##STR1054## 4-Br                                                                               H   2-Br                                                                               H                                             B-41                                                                                    ##STR1055## 4-Cl                                                                               H   H   H                                             B-42                                                                                    ##STR1056## H   H   2-Br                                                                               H                                             __________________________________________________________________________

                  TABLE 33                                                         ______________________________________                                          ##STR1057##                                                                   X.sup.5 : = O                                                                  Compound No.  P               R.sup.23                                         ______________________________________                                         CI-1          1               CH.sub.3                                         CI-2          1               CF.sub.3                                         CI-3          1               NO.sub.2                                         CI-4          2               Cl                                               CI-5          2               CH.sub.3                                         ______________________________________                                    

                  TABLE 34                                                         ______________________________________                                          ##STR1058##                                                                   Compound No. P     R.sup.23 R.sup.24                                           ______________________________________                                         CII-1        0     --                                                                                       ##STR1059##                                       CII-2        0     --                                                                                       ##STR1060##                                       CII-3        0     --                                                                                       ##STR1061##                                       CII-4        0     --                                                                                       ##STR1062##                                       CII-5        0     --                                                                                       ##STR1063##                                       CII-6        0     --                                                                                       ##STR1064##                                       CII-7        0     --                                                                                       ##STR1065##                                       CII-8        0     --                                                                                       ##STR1066##                                       CII-9        0     --                                                                                       ##STR1067##                                       CII-10       0     --                                                                                       ##STR1068##                                       CII-11       0     --                                                                                       ##STR1069##                                       CII-12       0     --                                                                                       ##STR1070##                                       CII-13       0     --                                                                                       ##STR1071##                                       CII-14       0     --                                                                                       ##STR1072##                                       CII-15       0     --                                                                                       ##STR1073##                                       CII-16       0     --                                                                                       ##STR1074##                                       CII-17       0     --                                                                                       ##STR1075##                                       CII-18       0     --                                                                                       ##STR1076##                                       CII-19       0     --                                                                                       ##STR1077##                                       CII-20       0     --                                                                                       ##STR1078##                                       CII-21       0     --                                                                                       ##STR1079##                                       CII-22       0     --                                                                                       ##STR1080##                                       CII-23       0     --                                                                                       ##STR1081##                                       CII-24       1     CF.sub.3                                                                                 ##STR1082##                                       CII-25       1     CF.sub.3                                                                                 ##STR1083##                                       CII-26       1     CF.sub.3                                                                                 ##STR1084##                                       CII-27       1     CF.sub.3                                                                                 ##STR1085##                                       CII-28       1     CF.sub.3                                                                                 ##STR1086##                                       CII-29       1     CF.sub.3                                                                                 ##STR1087##                                       CII-30       1     CF.sub.3                                                                                 ##STR1088##                                       CII-31       1     NO.sub.2                                                                                 ##STR1089##                                       CII-32       1     NO.sub.2                                                                                 ##STR1090##                                       CII-33       1     NO.sub.2                                                                                 ##STR1091##                                       CII-34       1     NO.sub.2                                                                                 ##STR1092##                                       CII-35       1     NO.sub.2                                                                                 ##STR1093##                                       CII-36       1     NO.sub.2                                                                                 ##STR1094##                                       CII-37       2     CH.sub.3                                                                                 ##STR1095##                                       CII-38       2     CH.sub.3                                                                                 ##STR1096##                                       CII-39       2     CH.sub.3                                                                                 ##STR1097##                                       CII-40       2     CH.sub.3                                                                                 ##STR1098##                                       CII-41       2     CH.sub.3                                                                                 ##STR1099##                                       CII-42       2     Cl                                                                                       ##STR1100##                                       CII-43       2     Cl                                                                                       ##STR1101##                                       CII-44       2     Cl                                                                                       ##STR1102##                                       CII-45       2     Cl                                                                                       ##STR1103##                                       ______________________________________                                    

                                      TABLE 35                                     __________________________________________________________________________      ##STR1104##                                                                   Compound No.                                                                           P R.sup.23                                                                          R.sup.25     R.sup.26                                             __________________________________________________________________________     CIII-1  0 -- H            CN                                                   CIII-2  0 -- H            COOC.sub.2 H.sub.5                                   CIII-3  0 -- H            COOC.sub.4 H.sub.9                                   CIII-4  0 -- H                                                                                            ##STR1105##                                         CIII-5  0 -- H                                                                                            ##STR1106##                                         CIII-6  0 -- H                                                                                            ##STR1107##                                         CIII-7  0 -- CN           CN                                                   CIII-8  0 -- CN           COOCH.sub.3                                          CIII-9  0 -- CN           COOC.sub.2 H.sub.5                                   CIII-10 0 -- CN           COOC.sub.3 H.sub.7                                   CIII-11 0 -- CN           COOC.sub.4 H.sub.9                                   CIII-12 0 -- CN           COOC.sub.5 H.sub.11                                  CIII-13 0 -- CN           COOC.sub.6 H.sub.13                                  CIII-14 0 -- CN           COOC.sub.7 H.sub.15                                  CIII-15 0 -- CN           COOC.sub.8 H.sub.17                                  CIII-16 0 -- CN           COOCF.sub.3                                          CIII-17 0 -- CN           COOCH(CF.sub.3).sub.2                                CIII-18 0 -- CN           COOCH.sub.2 OCH.sub.3                                CIII-19 0 -- CN           COOC.sub.2 H.sub.4 OCH.sub.3                         CIII-20 0 -- CN                                                                                           ##STR1108##                                         CIII-21 0 -- CN                                                                                           ##STR1109##                                         CIII-22 0 -- CN                                                                                           ##STR1110##                                         CIII-23 0 -- CN                                                                                           ##STR1111##                                         CIII-24 0 -- CN                                                                                           ##STR1112##                                         CIII-25 0 -- CN                                                                                           ##STR1113##                                         CIII-26 0 -- CN                                                                                           ##STR1114##                                         CIII-27 0 -- CN                                                                                           ##STR1115##                                         CIII-28 0 -- CN                                                                                           ##STR1116##                                         CIII-29 0 -- CN                                                                                           ##STR1117##                                         CIII-30 0 -- CN                                                                                           ##STR1118##                                         CIII-31 0 -- CN                                                                                           ##STR1119##                                         CIII-32 0 -- CN                                                                                           ##STR1120##                                         CIII-33 0 -- CN                                                                                           ##STR1121##                                         CIII-34 0 -- CN                                                                                           ##STR1122##                                         CIII-35 0 -- CN                                                                                           ##STR1123##                                         CIII-36 0 -- CN                                                                                           ##STR1124##                                         CIII-37 0 -- CN                                                                                           ##STR1125##                                         CIII-38 0 -- CN                                                                                           ##STR1126##                                         CIII-39 0 -- CN                                                                                           ##STR1127##                                         CIII-40 0 -- CN                                                                                           ##STR1128##                                         CIII-41 0 -- CN                                                                                           ##STR1129##                                         CIII-42 0 -- CN                                                                                           ##STR1130##                                         CIII-43 0 -- CN                                                                                           ##STR1131##                                         CIII-44 0 -- CN                                                                                           ##STR1132##                                         CIII-45 0 -- CN                                                                                           ##STR1133##                                         CIII-46 0 -- COOCH.sub.3  COOCH.sub.3                                          CIII-47 0 -- COOCH.sub.3                                                                                  ##STR1134##                                         CIII-48 0 -- COOC.sub.2 H.sub.5                                                                          COOC.sub.2 H.sub.5                                   CIII-49 0 -- COOCH(CH.sub.3).sub.2                                                                       COOCH(CH.sub.3).sub.2                                CIII-50 0 -- COOC.sub.4 H.sub.9                                                                          COOC.sub.4 H.sub.9                                   CIII-51 0 --                                                                                 ##STR1135##                                                                                 ##STR1136##                                         CIII-52 1 CF.sub.3                                                                          H            CN                                                   CIII-53 1 CF.sub.3                                                                          H            COOC.sub.4 H.sub.9                                   CIII-54 1 CF.sub.3                                                                          H                                                                                            ##STR1137##                                         CIII-55 1 CF.sub.3                                                                          CN           CN                                                   CIII-56 1 CF.sub.3                                                                          CN           COOC.sub.2 H.sub.5                                   CIII-57 1 CF.sub.3                                                                          CN           COOC.sub.4 H.sub.9                                   CIII-58 1 CF.sub.3                                                                          CN           COOC.sub.6 H.sub.13                                  CIII-59 1 CF.sub.3                                                                          CN           COOC.sub.8 H.sub.17                                  CIII-60 1 CF.sub.3                                                                          CN                                                                                           ##STR1138##                                         CIII-61 1 CF.sub.3                                                                          CN                                                                                           ##STR1139##                                         CIII-62 1 CF.sub.3                                                                          CN                                                                                           ##STR1140##                                         CIII-63 1 CF.sub.3                                                                          COOC.sub.2 H.sub.5                                                                          COOC.sub.2 H.sub.5                                   CIII-64 1 CF.sub.3                                                                          COOC.sub.4 H.sub.9                                                                          COOC.sub.4 H.sub.9                                   CIII-65 1 NO.sub.2                                                                          CN           CN                                                   CIII-66 1 NO.sub.2                                                                          CN           COOC.sub.4 H.sub.9                                   CIII-67 1 NO.sub.2                                                                          CN           COOC.sub.6 H.sub.13                                  CIII-68 1 NO.sub.2                                                                          CN           COOC.sub.8 H.sub.17                                  CIII-69 1 NO.sub.2                                                                          CN                                                                                           ##STR1141##                                         CIII-70 I NO.sub.2                                                                          CN                                                                                           ##STR1142##                                         CIII-71 1 NO.sub.2                                                                          COOC.sub.2 H.sub.5                                                                          COOC.sub.2 H.sub.5                                   CIII-72 1 NO.sub.2                                                                          COOC.sub.4 H.sub.9                                                                          COOC.sub.4 H.sub.9                                   CIII-73 2 CH.sub.3                                                                          CN           CN                                                   CIII-74 2 CH.sub.3                                                                          CN           COOC.sub.4 H.sub.9                                   CIII-75 2 CH.sub.3                                                                          CN           COOC.sub.6 H.sub.13                                  CIII-76 2 CH.sub.3                                                                          CN           COOC.sub.8 H.sub.17                                  CIII-77 2 CH.sub.3                                                                          CN                                                                                           ##STR1143##                                         CIII-78 2 CH.sub.3                                                                          CN                                                                                           ##STR1144##                                         CIII-79 2 CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                          COOC.sub.2 H.sub.5                                   CIII-80 2 CH.sub.3                                                                          COOC.sub.4 H.sub.9                                                                          COOC.sub.4 H.sub.9                                   CIII-81 2 Cl CN           CN                                                   CIII-82 2 Cl CN           COOC.sub.4 H.sub.9                                   CIII-83 2 Cl CN           COOC.sub.6 H.sub.13                                  CIII-84 2 Cl CN           COOC.sub.8 H.sub.17                                  CIII-85 2 Cl CN                                                                                           ##STR1145##                                         CIII-86 2 Cl CN                                                                                           ##STR1146##                                         CIII-87 2 Cl COOC.sub.2 H.sub.5                                                                          COOC.sub.2 H.sub.5                                   CIII-88 2 Cl COOC.sub.4 H.sub.9                                                                          COOC.sub.4 H.sub.9                                   __________________________________________________________________________

It is also preferable that the organic acceptor compound for use in the present invention have a reduction potential in a range of -0.2 to -1.2 V (vs SCE).

As organic acceptor compounds having a reduction potential in the above-mentioned range, derivatives of benzoquinone, naphthoquinone, anthraquinone, diphenoquinone; anhydrides; and aliphatic compounds, aromatic compound, and heterocyclic compounds, which have an electron attractive group such as nitro group, nitroso group, or cyano group, can be given.

The reduction potential of such organic acceptor compounds for use in the present invention is a half-wave potential obtained by conventionally known cyclic voltametry, using acetonitrile as a solvent, 0.1 MTEAP as an electrolyte, and a saturated calomel electrode (SCE) as a reference electrode.

The reasons why it is preferable that the organic acceptor compound for use in the present invention have a reduction potential in a range of -0.2 to -1.2 V (vs SCE) are that the reduction potential corresponds to the affinity for electrons, and that organic acceptor compounds with a reduction potential in the above-mentioned range have excellent electron transporting performance, so that when the organic acceptor compounds with a reduction potential in the above-mentioned range are employed in combination with the disazo compound and trisazo compound having the previously mentioned respective chemical structures, which are used as charge generating materials, excellent electrophotographic characteristics are exhibited.

The above-mentioned organic acceptor compounds can be used alone or in combination.

Furthermore in the present invention, to improve the charging stability of the single-layered photoconductive layer during the repeated use thereof, the photoconductive layer may further comprise an antioxidant.

More specifically, any conventional antioxidants can be employed. Specific examples of such antioxidants include antioxidants for plastics, rubber, petroleum, and fats and oils; ultraviolet absorbers; and light stabilizers such as phenol and phenol derivatives, paraphenylenediamines, hydroquinone and derivatives thereof, organic sulfur-containing compounds, organic phosphorus-containing compounds, hydroxy anisoles, piperidine and oxopiperidine, carotenes, amines, tocophenols, Ni(II) complexes, and sulfides, as disclosed in Japanese Laid-Open Patent Applications 57-122444, 60-188956, 63-18355, and 63-18356.

In particular, It is preferable that such an antioxidant for use in the present invention comprise at least one compound selected from the group consisting of compounds of formulae (I) to (XII):

[Compound of Formula (I)] ##STR1147## wherein R¹, R², R³ and R⁴ each is hydrogen, a halogen atom, hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted amino group, imino group, a heterocyclic group, a sulfoxide group, a sulfonyl group, an acyl group, or an azo group.

[Compound of Formula (II)] ##STR1148## wherein R¹, R², R³ and R⁴ each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, an alkylthio group, an arylthio group, an alkylamino group, an arylamino group, an acyl group, an alkylacylamino group, an arylacylamino group, an alkylcarbamoyl group, an arylcarbamoyl group, an alkylsulfonamide group, an arylsulfonamide group, an alkylsulfamoyl group, an arylsulfamoyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, an alkylacyloxy group, an arylacyloxy group, a silyl group, or a heterocyclic group, provided that at least one of R¹, R², R³ or R⁴ is a group having 4 or more carbon atoms.

[Compound of Formula (III)] ##STR1149## wherein R¹ to R⁸ each is hydrogen, a hydroxyl group, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted phosphonyl group, or a substituted or unsubstituted carbamoyl group.

[Compound of Formula (IV)] ##STR1150## wherein R¹ to R⁷ each is hydrogen, a hydroxyl group, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted phosphonyl group, or a substituted or unsubstituted carbamoyl group.

[Compound of Formula (V)] ##STR1151## wherein R¹ to R⁷ each is hydrogen, a hydroxyl group, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted phosphonyl group, or a substituted or unsubstituted carbamoyl group.

[Compound of Formula (VI)] ##STR1152## wherein R¹ to R⁶ each is hydrogen, a hydroxyl group, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted phosphonyl group, or a substituted or unsubstituted carbamoyl group.

[Compound of Formula (VII)] ##STR1153## wherein R¹ to R⁸ each is hydrogen, a hydroxyl group, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted phosphonyl group, or a substituted or unsubstituted carbamoyl group.

[Compound of Formula (VIII)] ##STR1154## [Compound of Formula (IX)] ##STR1155## wherein R¹ to R¹⁰ and R¹¹ to R¹⁸ each is hydrogen, a halogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted amino group, an imino group, a heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a sulfoxide group, a sulfonyl group, an acyl group, or an azo group.

[Compound of Formula (X)] ##STR1156## [Compound of Formula (XI)] ##STR1157## wherein R¹ to R⁸ and R⁹ to R¹⁸ each is hydrogen, a halogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted amino group, an imino group, a heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a sulfoxide group, a sulfonyl group, an acyl group, or an azo group.

[Compound of Formula (XII)] ##STR1158## wherein R¹ to R⁵ each is hydrogen, a halogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted amino group, an imino group, a heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a sulfoxide group, a sulfonyl group, an acyl group, or an azo group.

These antioxidants can be obtained by the synthesis in accordance with the methods described in U.S. Pat. No. 1,968,906 and J. Am. Chem. Soc. 55. 1224 (1933).

It is preferable that the amount of the antioxidant in the photoconductive layer be in the range of 0.01 to 2 parts by weight to 10 parts by weight of the binder resin. When the amount of the antioxidant is within the above range, the charging stability is sufficiently improved, with the decrease of photosensitivity and the increase of the residual potential being prevented.

TABLES 36 to 47 respectively show specific examples of the compounds of formulae (I) to (XII) serving as antioxidant component for use in the present invention.

                  TABLE 36                                                         ______________________________________                                          ##STR1159##                 (I)-1                                              ##STR1160##                 (I)-2                                              ##STR1161##                 (I)-3                                              ##STR1162##                 (I)-4                                              ##STR1163##                 (I)-5                                              ##STR1164##                 (I)-6                                              ##STR1165##                 (I)-7                                              ##STR1166##                 (I)-8                                              ##STR1167##                 (I)-9                                              ##STR1168##                 (I)-10                                             ##STR1169##                 (I)-11                                             ##STR1170##                 (I)-12                                             ##STR1171##                 (I)-13                                             ##STR1172##                 (I)-14                                             ##STR1173##                 (I)-15                                            ______________________________________                                    

                                      TABLE 37                                     __________________________________________________________________________      ##STR1174##              (II)-1                                                                               ##STR1175##               (II)-2                ##STR1176##              (II)-3                                                                               ##STR1177##               (II)-4                ##STR1178##              (II)-5                                                                               ##STR1179##               (II)-6                ##STR1180##              (II)-7                                                                               ##STR1181##               (II)-8                ##STR1182##              (II)-9                                                                               ##STR1183##               (II)-10               ##STR1184##              (II)-11                                                                              ##STR1185##               (II)-12               ##STR1186##              (II)-13                                                                              ##STR1187##               (II)-14               ##STR1188##              (II)-15                                                                              ##STR1189##               (II)-16               ##STR1190##              (II)-17                                                                              ##STR1191##               (II)-18               ##STR1192##              (II)-19                                                                              ##STR1193##               (II)-20               ##STR1194##              (II)-21                                                                              ##STR1195##               (II)-22               ##STR1196##              (II)-23                                                                              ##STR1197##               (II)-24               ##STR1198##              (II)-25                                                                              ##STR1199##               (II)-26               ##STR1200##              (II)-27                                                                              ##STR1201##               (II)-28               ##STR1202##              (II)-29                                                                              ##STR1203##               (II)-30               ##STR1204##              (II)-31                                                                              ##STR1205##               (II)-32               ##STR1206##              (II)-33                                                                              ##STR1207##               (II)-34               ##STR1208##              (II)-35                                                                              ##STR1209##               (II)-36               ##STR1210##              (II)-37                                                                              ##STR1211##               (II)-38               ##STR1212##                                              (II)-39               ##STR1213##                                              (II)-40               ##STR1214##              (II)-41                                                                              ##STR1215##               (II)-42               ##STR1216##              (II)-43                                                                              ##STR1217##               (II)-44               ##STR1218##              (II)-45                                                                              ##STR1219##               (II)-46               ##STR1220##                                              (II)-47               ##STR1221##              (II)-48                                                                              ##STR1222##               (II)-49               ##STR1223##              (II)-50                                                                              ##STR1224##               (II)-51               ##STR1225##              (II)-52                                                                              ##STR1226##               (II)-53               ##STR1227##              (II)-54                                                                              ##STR1228##               (II)-55               ##STR1229##              (II)-56                                                                              ##STR1230##               (II)-57               ##STR1231##              (II)-58                                                                              ##STR1232##               (II)-59               ##STR1233##              (II)-60                                                                              ##STR1234##               (II)-61               ##STR1235##              (II)-62                                                                              ##STR1236##               (II)-63               ##STR1237##              (II)-64                                                                              ##STR1238##               (II)-65               ##STR1239##              (II)-66                                                                              ##STR1240##               (II)-67               ##STR1241##              (II)-68                                                                              ##STR1242##               (II)-69               ##STR1243##              (II)-70                                                                              ##STR1244##               (II)-71               ##STR1245##              (II)-72                                                                              ##STR1246##               (II)-73               ##STR1247##              (II)-74                                                                              ##STR1248##               (II)-75               ##STR1249##              (II)-76                                                                              ##STR1250##               (II)-77               ##STR1251##              (II)-78                                                                              ##STR1252##               (II)-79               ##STR1253##              (II)-80                                                                              ##STR1254##               (II)-81               ##STR1255##              (II)-82                                                                              ##STR1256##               (II)-83               ##STR1257##              (II)-84                                                                              ##STR1258##               (II)-85               ##STR1259##              (II)-86                                                                              ##STR1260##               (II)-87               ##STR1261##              (II)-88                                                                              ##STR1262##               (II)-89               ##STR1263##              (II)-90                                                                              ##STR1264##               (II)-91               ##STR1265##              (II)-92                                                                              ##STR1266##               (II)-93               ##STR1267##              (II)-94                                                                              ##STR1268##               (II)-95               ##STR1269##                                              (II)-96               ##STR1270##              (II)-97                                                                              ##STR1271##               (II)-98               ##STR1272##              (II)-99                                                                              ##STR1273##               (II)-100              ##STR1274##              (II)-101                                                                             ##STR1275##               (II)-102              ##STR1276##              (II)-103                                                                             ##STR1277##               (II)-104              ##STR1278##              (II)-105                                                                             ##STR1279##               (II)-106              ##STR1280##              (II)-107                                                                             ##STR1281##               (II)-108              ##STR1282##              (II)-109                                                                             ##STR1283##               (II)-110              ##STR1284##              (II)-111                                                                             ##STR1285##               (II)-112              ##STR1286##              (II)-113                                                                             ##STR1287##               (II)-114              ##STR1288##              (II)-115                                                                             ##STR1289##               (II)-116              ##STR1290##              (II)-117                                                                             ##STR1291##               (II)-118              ##STR1292##              (II)-119                                                                             ##STR1293##               (II)-120              ##STR1294##              (II)-121                                                                             ##STR1295##               (II)-122              ##STR1296##              (II)-123                                                                             ##STR1297##               (II)-124              ##STR1298##              (II)-125                                                                             ##STR1299##               (II)-126              ##STR1300##              (II)-127                                                                             ##STR1301##               (II)-128              ##STR1302##              (II)-129                                                                             ##STR1303##               (II)-130              ##STR1304##              (II)-131                                                                             ##STR1305##               (II)-132              ##STR1306##              (II)-133                                                                             ##STR1307##               (II)-134              ##STR1308##              (II)-135                                                                             ##STR1309##               (II)-136              ##STR1310##              (II)-137                                                                             ##STR1311##               (II)-138              ##STR1312##              (II)-139                                                                             ##STR1313##               (II)-140              ##STR1314##              (II)-141                                                                             ##STR1315##               (II)-142              ##STR1316##              (II)-143                                                                             ##STR1317##               (II)-144              ##STR1318##              (II)-145                                                                             ##STR1319##               (II)-146              ##STR1320##              (II)-147                                                                             ##STR1321##               (II)-148              ##STR1322##              (II)-149                                                                             ##STR1323##               (II)-150              ##STR1324##              (II)-151                                                                             ##STR1325##               (II)-152              ##STR1326##              (II)-153                                                                             ##STR1327##               (II)-154              ##STR1328##              (II)-155                                                                             ##STR1329##               (II)-156              ##STR1330##              (II)-157                                                                             ##STR1331##               (II)-158              ##STR1332##              (II)-159                                                                             ##STR1333##               (II)-160              ##STR1334##              (II)-161                                                                             ##STR1335##               (II)-162              ##STR1336##              (II)-163                                                                             ##STR1337##               (II)-164              ##STR1338##              (II)-165                                                                             ##STR1339##               (II)-166              ##STR1340##              (II)-167                                                                             ##STR1341##               (II)-168              ##STR1342##              (II)-169                                                                             ##STR1343##               (II)-170              ##STR1344##              (II)-171                                                                             ##STR1345##               (II)-172              ##STR1346##              (II)-173                                                                             ##STR1347##               (II)-174              ##STR1348##              (II)-175                                                                             ##STR1349##               (II)-176              ##STR1350##              (II)-177                                                                             ##STR1351##               (II)-178              ##STR1352##              (II)-179                                                                             ##STR1353##               (II)-180              ##STR1354##              (II)-181                                                                             ##STR1355##               (II)-182              ##STR1356##              (II)-183                                                                             ##STR1357##               (II)-184              ##STR1358##              (II)-185                                                                             ##STR1359##               (II)-186              ##STR1360##              (II)-187                                                                             ##STR1361##               (II)-188              ##STR1362##              (II)-189                                                                             ##STR1363##               (II)-190              ##STR1364##              (II)-191                                                                             ##STR1365##               (II)-192              ##STR1366##              (II)-193                                                                             ##STR1367##               (II)-194              ##STR1368##              (II)-195                                                                             ##STR1369##               (II)-196              ##STR1370##              (II)-197                                                                             ##STR1371##               (II)-198              ##STR1372##              (II)-199                                                                             ##STR1373##               (II)-200              ##STR1374##              (II)-201                                                                             ##STR1375##               (II)-202              ##STR1376##              (II)-203                                                                             ##STR1377##               (II)-204              ##STR1378##              (II)-205                                                                             ##STR1379##               (II)-206              ##STR1380##              (II)-207                                                                             ##STR1381##               (II)-208              ##STR1382##              (II)-209                                                                             ##STR1383##               (II)-210              ##STR1384##              (II)-211                                                                             ##STR1385##               (II)-212              ##STR1386##              (II)-213                                                                             ##STR1387##               (II)-214              ##STR1388##                                              (II)-215              ##STR1389##                                              (II)-216              ##STR1390##                                              (II)-217              ##STR1391##                                              (II)-218              ##STR1392##                                              (II)-219              ##STR1393##                                              (II)-220              ##STR1394##                                              (II)-221              ##STR1395##                                              (II)-222              ##STR1396##              (II)-223                                                                             ##STR1397##               (II)-224             __________________________________________________________________________

                                      TABLE 38                                     __________________________________________________________________________      ##STR1398##                                               (III)-1              ##STR1399##                                               (III)-2              ##STR1400##                                               (III)-3              ##STR1401##                                               (III)-4              ##STR1402##                                               (III)-5              ##STR1403##                                               (III)-6              ##STR1404##                                               (III)-7              ##STR1405##                                               (III)-8              ##STR1406##                                               (III)-9              ##STR1407##                                               (III)-10             ##STR1408##                                               (III)-11             ##STR1409##                                               (III)-12             ##STR1410##                                               (III)-13             ##STR1411##                                               (III)-14             ##STR1412##                                               (III)-15             ##STR1413##                                               (III)-16             ##STR1414##                                               (III)-17             ##STR1415##                                               (III)-18             ##STR1416##                                               (III)-19             ##STR1417##                                               (III)-20             ##STR1418##                                               (III)-21             ##STR1419##                                               (III)-22             ##STR1420##                                               (III)-23             ##STR1421##                                               (III)-24             ##STR1422##                                               (III)-25             ##STR1423##                                               (III)-26             ##STR1424##                                               (III)-27             ##STR1425##                                               (III)-28             ##STR1426##                                               (III)-29             ##STR1427##                                               (III)-30             ##STR1428##                                               (III)-31             ##STR1429##                                               (III)-32             ##STR1430##                                               (III)-33             ##STR1431##                                               (III)-34             ##STR1432##                                               (III)-35             ##STR1433##                                               (III)-36             ##STR1434##                                               (III)-37             ##STR1435##                                               (III)-38             ##STR1436##                                               (III)-39             ##STR1437##                                               (III)-40             ##STR1438##                                               (III)-41             ##STR1439##                                               (III)-42             ##STR1440##                                               (III)-43             ##STR1441##                                               (III)-44             ##STR1442##                                               (III)-45             ##STR1443##                                               (III)-46             ##STR1444##                                               (III)-47             ##STR1445##                                               (III)-48            __________________________________________________________________________

                  TABLE 39                                                         ______________________________________                                          ##STR1446##                 (IV)-1                                             ##STR1447##                 (IV)-2                                             ##STR1448##                 (IV)-3                                             ##STR1449##                 (IV)-4                                             ##STR1450##                 (IV)-5                                             ##STR1451##                 (IV)-6                                             ##STR1452##                 (IV)-7                                             ##STR1453##                 (IV)-8                                             ##STR1454##                 (IV)-9                                             ##STR1455##                 (IV)-10                                            ##STR1456##                 (IV)-11                                            ##STR1457##                 (IV)-12                                            ##STR1458##                 (IV)-13                                           ______________________________________                                    

                                      TABLE 40                                     __________________________________________________________________________     Com-                                                                           pound                                                                          No. R.sup.1          R.sup.2                                                                               R.sup.3             R.sup.4                        __________________________________________________________________________     (V)-1                                                                              H                H                                                                                      ##STR1459##        H                              (V)-2                                                                              CH.sub.2 CH.sub.2 NH.sub.2                                                                      CH.sub.3                                                                              H                   H                              (V)-3                                                                               ##STR1460##            CH.sub.3            H                              (V)-4                                                                              H                H      H                   H                              (V)-5                                                                              CH.sub.2 CH.sub.2 NH.sub.2                                                                      CH.sub.3                                                                              H                   H                              (V)-6                                                                               ##STR1461##     CH.sub.3                                                                              H                   H                              (V)-7                                                                               ##STR1462##     CH.sub.3                                                                              H                   H                              (V)-8                                                                               ##STR1463##     CH.sub.3                                                                              H                   H                              (V)-9                                                                              CH.sub.2 CH.sub.2 Br                                                                            CH.sub.3                                                                              H                   H                              (V)-10                                                                             H                H      H                   H                              (V)-11                                                                             H                H      H                   H                              (V)-12                                                                             CH.sub.3         CH.sub.3                                                                              H                   CH.sub.3                       (V)-13                                                                             CH.sub.2 CH.sub.2 Cl                                                                            CH.sub.3                                                                              H                   H                              (V)-14                                                                              ##STR1464##     CH.sub.3                                                                              H                   H                              (V)-15                                                                             H                H      H                   H                              (V)-16                                                                             H                H      H                   H                              (V)-17                                                                             H                H      H                   H                              (V)-18                                                                             H                H      H                   H                              (V)-19                                                                             CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-20                                                                             CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-21                                                                             CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-22                                                                             CH.sub.3         CH.sub.3                                                                              H                                                                                                   ##STR1465##                   (V)-23                                                                             CH.sub.3         CH.sub.3                                                                              H                                                                                                   ##STR1466##                   (V)-24                                                                             CH.sub.3         CH.sub.3                                                                              H                                                                                                   ##STR1467##                   (V)-25                                                                              ##STR1468##     CH.sub.3                                                                              H                   H                              (V)-26                                                                              ##STR1469##     CH.sub.3                                                                              H                   H                              (V)-27                                                                              ##STR1470##     CH.sub.3                                                                              H                   H                              (V)-28                                                                              ##STR1471##     CH.sub.3                                                                              H                   H                              (V)-29                                                                              ##STR1472##     CH.sub.3                                                                              H                   H                              (V)-30                                                                              ##STR1473##     CH.sub.3                                                                              H                   H                              (V)-31                                                                             H                H                                                                                      ##STR1474##        H                              (V)-32                                                                              ##STR1475##     CH.sub.3                                                                              H                   H                              (V)-33                                                                             H                H      H                   H                              (V)-34                                                                             H                H      H                   H                              (V)-35                                                                             H                H      H                   H                              (V)-36                                                                             H                H      H                   H                              (V)-37                                                                             H                H      H                   H                              (V)-38                                                                             CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-39                                                                             H                H                                                                                      ##STR1476##        H                              (V)-40                                                                             H                H                                                                                      ##STR1477##        H                              (V)-41                                                                             OCH.sub.3        CH.sub.3                                                                              H                   H                              (V)-42                                                                              ##STR1478##     CH.sub.3                                                                              H                   H                              (V)-43                                                                              ##STR1479##     CH.sub.3                                                                              H                   H                              (V)-44                                                                              ##STR1480##     CH.sub.3                                                                              H                   H                              (V)-45                                                                              ##STR1481##     CH.sub.3                                                                              H                   H                              (V)-46                                                                              ##STR1482##     CH.sub.3                                                                              H                   H                              (V)-47                                                                              ##STR1483##     CH.sub.3                                                                              H                   H                              (V)-48                                                                              ##STR1484##     CH.sub.3                                                                              H                   H                              (V)-49                                                                             CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-50                                                                             H                H      H                   CH.sub.3                       (V)-51                                                                             H                H                                                                                      ##STR1485##        H                              (V)-52                                                                             H                H      H                   H                              (V)-53                                                                             H                H      H                   H                              (V)-54                                                                             H                H      H                   H                              (V)-55                                                                             H                H      H                   H                              (V)-56                                                                             H                H      H                   H                              (V)-57                                                                             H                H      H                   H                              (V)-58                                                                             H                H      H                   H                              (V)-59                                                                             H                H      H                                                                                                   ##STR1486##                   (V)-60                                                                             CH.sub.3         CH.sub.3                                                                              H                   CH.sub.3                       (V)-61                                                                             CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-62                                                                             CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-63                                                                             CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-64                                                                             CH.sub.3         H      H                   H                              (V)-65                                                                              ##STR1487##     CH.sub.3                                                                              H                   H                              (V)-66                                                                              ##STR1488##     CH.sub.3                                                                              H                   H                              (V)-67                                                                             C.sub.3 H.sub.7 (n)                                                                             CH.sub.3                                                                              H                   H                              (V)-68                                                                              ##STR1489##     CH.sub.3                                                                              H                   H                              (V)-69                                                                              ##STR1490##     CH.sub.3                                                                              H                   H                              (V)-70                                                                              ##STR1491##     CH.sub.3                                                                              H                   H                              (V)-71                                                                              ##STR1492##     CH.sub.3                                                                              H                   H                              (V)-72                                                                              ##STR1493##     CH.sub.3                                                                              H                   H                              (V)-73                                                                              ##STR1494##     CH.sub.3                                                                              H                   H                              (V)-74                                                                             CH.sub.3         CH.sub.3                                                                              CH.sub.3            H                              (V)-75                                                                             CH.sub.3         H      H                   H                              (V)-76                                                                             H                H      H                   H                              (V)-77                                                                             CH.sub.3         CH.sub.3                                                                              H                   CH.sub.3                       (V)-78                                                                              ##STR1495##     CH.sub.3                                                                              H                   H                              (V)-79                                                                              ##STR1496##     CH.sub.3                                                                              H                   H                              (V)-80                                                                              ##STR1497##     CH.sub.3                                                                              H                   H                              (V)-81                                                                              ##STR1498##     CH.sub.3                                                                              H                   H                              (V)-82                                                                              ##STR1499##     CH.sub.3                                                                              H                   H                              (V)-83                                                                              ##STR1500##     CH.sub.3                                                                              H                   H                              (V)-84                                                                              ##STR1501##     CH.sub.3                                                                              H                   H                              (V)-85                                                                             CH(OCH.sub.3).sub.2                                                                             CH.sub.3                                                                              H                   H                              (V)-86                                                                             CH(OCH.sub.3).sub.2                                                                             H      H                   H                              (V)-87                                                                             CH.sub.2 CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                    CH.sub.3                                                                              H                   H                              (V)-88                                                                             CH.sub.2 CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                     ##STR1502##                                                                          H                   H                              (V)-89                                                                             CH.sub.2 CH.sub.2 OCH(CH.sub.3).sub.2                                                           CH.sub.3                                                                              H                   H                              (V)-90                                                                             CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-91                                                                             CH.sub.3         CH.sub.3                                                                              H                                                                                                   ##STR1503##                   (V)-92                                                                             C.sub.8 H.sub.17 (n)                                                                            CH.sub.3                                                                              H                                                                                                   ##STR1504##                   (V)-93                                                                             C.sub.8 H.sub.17 (n)                                                                            CH.sub.3                                                                              H                   H                              (V)-94                                                                             CH.sub.3         CH.sub.3                                                                              H                   CH.sub.3                       (V)-95                                                                             CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-96                                                                              ##STR1505##     CH.sub.3                                                                              H                   H                              (V)-97                                                                              ##STR1506##     C.sub.2 H.sub.5                                                                       H                   H                              (V)-98                                                                              ##STR1507##     C.sub.2 H.sub.5                                                                       H                   H                              (V)-99                                                                             CHCH.sub.2       CH.sub.3                                                                              H                   H                              (V)-100                                                                            C.sub.2 H.sub.5  CH.sub.3                                                                              H                   H                              (V)-101                                                                            C.sub.2 H.sub.5  H      H                   H                              (V)-102                                                                            C.sub.16 H.sub.33 (n)                                                                           CH.sub.3                                                                              H                   H                              (V)-103                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-104                                                                        (V)-105                                                                             ##STR1508##     CH.sub.3                                                                              H                   H                              (V)-106                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-107                                                                             ##STR1509##     CH.sub.3                                                                              H                   CH.sub.3                       (V)-108                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-109                                                                             ##STR1510##     H                                                                                      ##STR1511##        CH.sub.3                       (V)-110                                                                            CH.sub.3         CH.sub.3                                                                              H                                                                                                   ##STR1512##                   (V)-111                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-112                                                                             ##STR1513##     CH.sub.3                                                                              H                   H                              (V)-113                                                                             ##STR1514##     CH.sub.3                                                                              H                   H                              (V)-114                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-115                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-116                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-117                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-118                                                                             ##STR1515##     H      H                   H                              (V)-119                                                                            OCH.sub.3        CH.sub.3                                                                              H                   H                              (V)-120                                                                            OCH.sub.3        CH.sub.3                                                                              H                   H                              (V)-121                                                                             ##STR1516##     H      H                   H                              (V)-122                                                                            OCH.sub.3        H      H                   H                              (V)-123                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-124                                                                             ##STR1517##     CH.sub.3                                                                              H                   H                              (V)-125                                                                             ##STR1518##     CH.sub.3                                                                              H                   CH.sub.3                       (V)-126                                                                             ##STR1519##     CH.sub.3                                                                              H                   H                              (V)-127                                                                            C.sub.5 H.sub.11 (n)                                                                            CH.sub.3                                                                              H                   H                              (V)-128                                                                             ##STR1520##     CH.sub.3                                                                              H                   H                              (V)-129                                                                            C.sub.13 H.sub.27 (n)                                                                           CH.sub.3                                                                              H                   H                              (V)-130                                                                             ##STR1521##     CH.sub.3                                                                              H                   H                              (V)-131                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-132                                                                            CH.sub.3         CH.sub.3                                                                              H                   CH.sub.3                       (V)-133                                                                            CH.sub.3         CH.sub.3                                                                              H                   C.sub.8 H.sub.17 (n)           (V)-134                                                                            CH.sub.3         CH.sub.3                                                                              H                   CH.sub.3                       (V)-135                                                                             ##STR1522##     H      H                   H                              (V)-136                                                                             ##STR1523##     H                                                                                      ##STR1524##        H                              (V)-137                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-138                                                                            OCH.sub.3        CH.sub.3                                                                              H                   H                              (V)-139                                                                             ##STR1525##     CH.sub.3                                                                              H                   H                              (V)-140                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-141                                                                            H                H      OC.sub.2 H.sub.5    CH.sub.3                       (V)-142                                                                             ##STR1526##     CH.sub.3                                                                              H                   H                              (V)-143                                                                            CH.sub.3         H      H                                                                                                   ##STR1527##                   (V)-144                                                                            OC.sub.2 H.sub.5 CH.sub.3                                                                              H                   H                              (V)-145                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-146                                                                            OCH.sub.3        C.sub.2 H.sub.5                                                                       H                   H                              (V)-147                                                                            H                H                                                                                      ##STR1528##        OCH.sub.3                      (V)-148                                                                             ##STR1529##     H                                                                                      ##STR1530##        H                              (V)-149                                                                             ##STR1531##     H      C.sub.3 H.sub.7 (n) H                              (V)-150                                                                             ##STR1532##     H      OC.sub.2 H.sub.5    H                              (V)-151                                                                             ##STR1533##     CH.sub.3                                                                              H                   H                              (V)-152                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-153                                                                             ##STR1534##     CH.sub.3                                                                              H                   H                              (V)-154                                                                             ##STR1535##     CH.sub.3                                                                              H                   H                              (V)-155                                                                             ##STR1536##     CH.sub.3                                                                              H                   H                              (V)-156                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-157                                                                             ##STR1537##     CH.sub.3                                                                              H                   H                              (V)-158                                                                             ##STR1538##     CH.sub.3                                                                              H                   H                              (V)-159                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-160                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-161                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-162                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-163                                                                            H                H                                                                                      ##STR1539##        H                              (V)-164                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-165                                                                            C.sub.3 H.sub.7 (n)                                                                             CH.sub.3                                                                              H                   H                              (V)-166                                                                             ##STR1540##     CH.sub.3                                                                              H                   H                              (V)-167                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-168                                                                            C.sub.3 H.sub.7 (n)                                                                             CH.sub.3                                                                              H                   H                              (V)-169                                                                            OCH.sub.3        H      H                   CH.sub.3                       (V)-170                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-171                                                                             ##STR1541##     H                                                                                      ##STR1542##        H                              (V)-172                                                                             ##STR1543##     H      C.sub.3 H.sub.7 (n) H                              (V)-173                                                                            CH.sub.3         OCH.sub.3                                                                             H                   H                              (V)-174                                                                            CH.sub.3         H      H                   H                              (V)-175                                                                             ##STR1544##     CH.sub.3                                                                              H                   H                              (V)-176                                                                             ##STR1545##     CH.sub.3                                                                              H                   H                              (V)-177                                                                             ##STR1546##     CH.sub.3                                                                              H                   H                              (V)-178                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-179                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-180                                                                             ##STR1547##     CH.sub.3                                                                              H                   H                              (V)-181                                                                             ##STR1548##     CH.sub.3                                                                              H                   H                              (V)-182                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-183                                                                             ##STR1549##     CH.sub.3                                                                              H                   H                              (V)-184                                                                             ##STR1550##     CH.sub.3                                                                              H                   H                              (V)-185                                                                             ##STR1551##     CH.sub.3                                                                              H                   H                              (V)-186                                                                            C.sub.8 H.sub.17 (n)                                                                            CH.sub.3                                                                              H                   H                              (V)-187                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-188                                                                             ##STR1552##     CH.sub.3                                                                              H                   H                              (V)-189                                                                             ##STR1553##     CH.sub.3                                                                              H                   H                              (V)-190                                                                             ##STR1554##     CH.sub.3                                                                              H                   H                              (V)-191                                                                             ##STR1555##     OC.sub.2 H.sub.5                                                                      OCH.sub.3           H                              (V)-192                                                                             ##STR1556##     OCH.sub.3                                                                             OC.sub.2 H.sub.5    H                              (V)-193                                                                             ##STR1557##     H      OC.sub.2 H.sub.5    H                              (V)-194                                                                            OC.sub.2 H.sub.5 H      H                   CH.sub.3                       (V)-195                                                                            CH.sub.3         CH.sub.3                                                                              H                   H                              (V)-196                                                                            C.sub.2 H.sub.5  CH.sub.3                                                                              H                   H                              (V)-197                                                                             ##STR1558##     CH.sub.3                                                                              H                   H                              (V)-198                                                                             ##STR1559##     H      H                   H                              (V)-199                                                                             ##STR1560##     H      H                   H                              (V)-200                                                                             ##STR1561##     H      CH.sub.3            H                              (V)-201                                                                             ##STR1562##     H      CH.sub.3            H                              (V)-202                                                                             ##STR1563##     H      CH.sub.3            H                              (V)-203                                                                             ##STR1564##     H      H                   H                              (V)-204                                                                             ##STR1565##     H      CH.sub.3            H                              (V)-205                                                                             ##STR1566##     CH.sub.3                                                                              H                   H                              (V)-206                                                                            CH.sub.3         CH.sub.3                                                                               ##STR1567##        H                              (V)-207                                                                            CH.sub.3         CH.sub.3                                                                               ##STR1568##        H                              (V)-208                                                                            CH.sub.3         CH.sub.3                                                                               ##STR1569##        H                              (V)-209                                                                            CH.sub.3         CH.sub.3                                                                               ##STR1570##        H                              (V)-210                                                                              ##STR1571##                                                              (V)-211                                                                              ##STR1572##                                                              (V)-212                                                                              ##STR1573##                                                              (V)-213                                                                              ##STR1574##                                                              (V)-214                                                                              ##STR1575##                                                              (V)-215                                                                              ##STR1576##                                                              (V)-216                                                                              ##STR1577##                                                              (V)-217                                                                              ##STR1578##                                                              (V)-218                                                                              ##STR1579##                                                              (V)-219                                                                              ##STR1580##                                                              (V)-220                                                                              ##STR1581##                                                              (V)-221                                                                              ##STR1582##                                                              (V)-222                                                                              ##STR1583##                                                              (V)-223                                                                              ##STR1584##                                                              (V)-224                                                                              ##STR1585##                                                              (V)-225                                                                              ##STR1586##                                                              (V)-226                                                                              ##STR1587##                                                              (V)-227                                                                              ##STR1588##                                                              (V)-228                                                                              ##STR1589##                                                              (V)-229                                                                              ##STR1590##                                                              (V)-230                                                                              ##STR1591##                                                              (V)-231                                                                              ##STR1592##                                                              __________________________________________________________________________     Com-                                                                           pound                                                                          No. R.sup.5          R.sup.6        R.sup.7         R.sup.8                    __________________________________________________________________________     (V)-1                                                                              H                H              OCH.sub.3       OCH.sub.3                  (V)-2                                                                              H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-3                                                                              H                H              CH.sub.2 CH.sub.2 NH.sub.2                                                                     H                          (V)-4                                                                              H                H              CH.sub.2 CH.sub.2 NH.sub.2                                                                     H                          (V)-5                                                                              H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-6                                                                              H                CH.sub.2 CH.sub.2 NH.sub.2                                                                    CH.sub.3        CH.sub.3                   (V)-7                                                                              H                CH.sub.3       CH.sub.2 CH.sub.2 NH.sub.2                                                                     CH.sub.3                   (V)-8                                                                              H                CH.sub.2 CH.sub.2 NH.sub.2                                                                    CH.sub.2 CH.sub.2 NH.sub.2                                                                     CH.sub.3                   (V)-9                                                                              H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-10                                                                             H                                                                                                ##STR1593##   H               H                          (V)-11                                                                             H                H                                                                                              ##STR1594##    H                          (V)-12                                                                             CH.sub.3         H                                                                                              ##STR1595##    H                          (V)-13                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-14                                                                             H                H              H               H                          (V)-15                                                                             H                                                                                                ##STR1596##   H               H                          (V)-16                                                                             H                H                                                                                              ##STR1597##    H                          (V)-17                                                                             H                                                                                                ##STR1598##   H               H                          (V)-18                                                                             H                H                                                                                              ##STR1599##    H                          (V)-19                                                                             H                OCH.sub.3      OCH.sub.3       H                          (V)-20                                                                             H                H              H               H                          (V)-21                                                                             H                                                                                                ##STR1600##                                                                                   ##STR1601##    H                          (V)-22                                                                             H                H              H               H                          (V)-23                                                                             H                H              C.sub.8 H.sub.17 (n)                                                                           H                          (V)-24                                                                             H                H                                                                                              ##STR1602##    H                          (V)-25                                                                             H                CH.sub.3       H               H                          (V)-26                                                                             H                H              CH.sub.3        H                          (V)-27                                                                             H                H              H               CH.sub.3                   (V)-28                                                                             H                H              CH.sub.3        H                          (V)-29                                                                             H                CH.sub.3       H               H                          (V)-30                                                                             H                H              CH.sub.3        H                          (V)-31                                                                             H                H              OCH.sub.3       OCH.sub.3                  (V)-32                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-33                                                                             H                                                                                                ##STR1603##   H               H                          (V)-34                                                                             H                H                                                                                              ##STR1604##    H                          (V)-35                                                                             H                                                                                                ##STR1605##   H               H                          (V)-36                                                                             H                H                                                                                              ##STR1606##    H                          (V)-37                                                                             H                                                                                                ##STR1607##   H               H                          (V)-38                                                                             H                H              OCH.sub.3       H                          (V)-39                                                                             H                H              OCH.sub.3       H                          (V)-40                                                                             H                H              OCH.sub.3       H                          (V)-41                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-42                                                                             H                H              H               H                          (V)-43                                                                             H                H              H               H                          (V)-44                                                                             H                H              H               H                          (V)-45                                                                             H                H              H               H                          (V)-46                                                                             H                H              H               H                          (V)-47                                                                             H                H              H               H                          (V)-48                                                                             H                H              H               H                          (V)-49                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-50                                                                             CH.sub.3         CH.sub.3       CH.sub.3        CH.sub.3                   (V)-51                                                                             H                H              H               H                          (V)-52                                                                             H                                                                                                ##STR1608##   H               H                          (V)-53                                                                             H                H                                                                                              ##STR1609##    H                          (V)-54                                                                             H                                                                                                ##STR1610##   H               H                          (V)-55                                                                             H                H                                                                                              ##STR1611##    H                          (V)-56                                                                             H                H              H                                                                                               ##STR1612##               (V)-57                                                                             H                                                                                                ##STR1613##   H               H                          (V)-58                                                                             H                H                                                                                              ##STR1614##    H                          (V)-59                                                                             H                H              H               H                          (V)-60                                                                             H                H              CH.sub.3        H                          (V)-61                                                                             H                CH.sub.3       CH.sub.3        H                          (V)-62                                                                             H                CH.sub.3       H               CH.sub.3                   (V)-63                                                                             H                H              CH.sub.3        CH.sub.3                   (V)-64                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-65                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-66                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-67                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-68                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-69                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-70                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-71                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-72                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-73                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-74                                                                             H                H              H               H                          (V)-75                                                                             H                CH.sub.3       CH.sub.3        H                          (V)-76                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-77                                                                             H                H                                                                                              ##STR1615##    H                          (V)-78                                                                             H                H              CH.sub.3        CH.sub.3                   (V)-79                                                                             H                H              CH.sub.3        CH.sub.3                   (V)-80                                                                             H                H              CH.sub.3        CH.sub.3                   (V)-81                                                                             H                CH.sub.3       H               CH.sub.3                   (V)-82                                                                             H                CH.sub.3       H               CH.sub.3                   (V)-83                                                                             H                CH.sub.3       CH.sub.3        H                          (V)-84                                                                             H                H              CH.sub.3        CH.sub.3                   (V)-85                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-86                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-87                                                                             H                H              H               H                          (V)-88                                                                             H                H              H               H                          (V)-89                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-90                                                                             H                H              C.sub.4 H.sub.9 (t)                                                                            H                          (V)-91                                                                             H                H              C.sub.4 H.sub.9 (t)                                                                            H                          (V)-92                                                                             H                H              C.sub.4 H.sub.9 (t)                                                                            H                          (V)-93                                                                             H                H              C.sub.4 H.sub.9 (t)                                                                            H                          (V)-94                                                                             H                H              C.sub.4 H.sub.9 (t)                                                                            H                          (V)-95                                                                             H                CH.sub.3       C.sub.4 H.sub.9 (t)                                                                            H                          (V)-96                                                                             H                H              H               H                          (V)-97                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-98                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-99                                                                             H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-100                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-101                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-102                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                    ##STR1616##                                                                        ##STR1617##     H              CH.sub.3        CH.sub.3                   (V)-105                                                                            H                C.sub.4 H.sub.9 (t)                                                                           C.sub.4 H.sub.9 (t)                                                                            H                          (V)-106                                                                            H                                                                                                ##STR1618##   CH.sub.3        CH.sub.3                   (V)-107                                                                            CH.sub.3         H              H               H                          (V)-108                                                                            H                CH.sub.3       CH.sub.2 Cl     CH.sub.3                   (V)-109                                                                            H                H              OCH.sub.3       H                          (V)-110                                                                            H                H              SC.sub.18 H.sub.37 (n)                                                                         H                          (V)-111                                                                            H                H                                                                                              ##STR1619##    H                          (V)-112                                                                            H                H              H               CH.sub.3                   (V)-113                                                                            H                H              H               CH.sub.3                   (V)-114                                                                            H                                                                                                ##STR1620##   CH.sub.3        CH.sub.3                   (V)-115                                                                            H                                                                                                ##STR1621##   CH.sub.3        CH.sub.3                   (V)-116                                                                            H                                                                                                ##STR1622##   CH.sub.3        CH.sub.3                   (V)-117                                                                            H                                                                                                ##STR1623##   CH.sub.3        CH.sub.3                   (V)-118                                                                            H                H              OCH.sub.3       H                          (V)-119                                                                            H                H              H               H                          (V)-120                                                                            H                                                                                                ##STR1624##                                                                                   ##STR1625##    H                          (V)-121                                                                            H                H              OCH.sub.3       H                          (V)-122                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-123                                                                            OCH.sub.3        H              H               CH.sub.3                   (V)-124                                                                            H                H              SC.sub.8 H.sub.17 (n)                                                                          H                          (V)-125                                                                            CH.sub.3         H              CH.sub.3        H                          (V)-126                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-127                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-128                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-129                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-130                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-131                                                                            H                H              H               CH.sub.3                   (V)-132                                                                            H                H                                                                                              ##STR1626##    H                          (V)-133                                                                            H                CH.sub.3       H               H                          (V)-134                                                                            H                H              C.sub.8 H.sub.17 (n)                                                                           H                          (V)-135                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-136                                                                            H                OCH.sub.3      OCH.sub.3       H                          (V)-137                                                                            H                C.sub.4 H.sub.9 (t)                                                                           H               H                          (V)-138                                                                            H                H              C.sub.4 H.sub.9 (t)                                                                            H                          (V)-139                                                                            H                H              C.sub.4 H.sub.9 (t)                                                                            H                          (V)-140                                                                            H                C.sub.4 H.sub.9 (t)                                                                           CH.sub.3        H                          (V)-141                                                                            CH.sub.3         H              C.sub.4 H.sub.9 (t)                                                                            H                          (V)-142                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-143                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-144                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-145                                                                            H                CH.sub.2 OC.sub.2 H.sub.5                                                                     CH.sub.3        CH.sub.3                   (V)-146                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-147                                                                            H                H              OCH.sub.3       H                          (V)-148                                                                            H                H              OCH.sub.3       H                          (V)-149                                                                            H                H              H               H                          (V)-150                                                                            H                H              H               H                          (V)-151                                                                            H                CH.sub.2 N(CH.sub.3).sub.2                                                                    CH.sub.2 N(CH.sub.3).sub.2                                                                     CH.sub.3                   (V)-152                                                                            H                CH.sub.2 Cl    CH.sub.3        CH.sub.3                   (V)-153                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-154                                                                            H                C.sub.2 H.sub.5                                                                               C.sub.2 H.sub.5 CH.sub.3                   (V)-155                                                                            H                CH.sub.3       OCH.sub.3       OCH.sub.3                  (V)-156                                                                            H                CH.sub.3       OCH.sub.3       OCH.sub.3                  (V)-157                                                                            H                CH.sub.3       H                                                                                               ##STR1627##               (V)-158                                                                            H                CH.sub.3       H                                                                                               ##STR1628##               (V)-159                                                                            H                H                                                                                              ##STR1629##    H                          (V)-160                                                                            H                H              C.sub.4 H.sub.9 (n)                                                                            H                          (V)-161                                                                            H                H              H               C.sub.4 H.sub.9 (n)        (V)-162                                                                            H                H                                                                                              ##STR1630##    H                          (V)-163                                                                            H                OCH.sub.3      OCH.sub.3       H                          (V)-164                                                                            H                                                                                                ##STR1631##   CH.sub.3        CH.sub.3                   (V)-165                                                                            H                                                                                                ##STR1632##   CH.sub.3        CH.sub.3                   (V)-166                                                                            H                                                                                                ##STR1633##   CH.sub.3        CH.sub.3                   (V)-167                                                                            H                                                                                                ##STR1634##   CH.sub.3        CH.sub.3                   (V)-168                                                                            H                                                                                                ##STR1635##   CH.sub.3        CH.sub.3                   (V)-169                                                                            CH.sub.3         CH.sub.2 OCH.sub.3                                                                            CH.sub.3        CH.sub.3                   (V)-170                                                                            H                CH.sub.2 OCH.sub.3                                                                            CH.sub.3        CH.sub.3                   (V)-171                                                                            H                H              H               H                          (V)-172                                                                            H                H              H               H                          (V)-173                                                                            H                H              CH.sub.3        CH.sub.3                   (V)-174                                                                            H                H              H               H                          (V)-175                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-176                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-177                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-178                                                                            H                CH.sub.3       H               H                          (V)-179                                                                            H                H              CH.sub.3        H                          (V)-180                                                                            H                CH.sub.3                                                                                       ##STR1636##    CH.sub.3                   (V)-181                                                                            H                                                                                                ##STR1637##   CH.sub.3        CH.sub.3                   (V)-182                                                                            H                                                                                                ##STR1638##   CH.sub.3        CH.sub.3                   (V)-183                                                                            H                CH.sub.2 N(CH.sub.3).sub.2                                                                    H               CH.sub.3                   (V)-184                                                                            H                CH.sub.2 N(CH.sub.3).sub.2                                                                    CH.sub.3        CH.sub.3                   (V)-185                                                                            H                CH.sub.3       CH.sub.2 N(CH.sub.3).sub.2                                                                     CH.sub.3                   (V)-186                                                                            H                H              C.sub.4 H.sub.9 (t)                                                                            H                          (V)-187                                                                            H                CH.sub.3       H               C.sub.4 H.sub.9 (t)        (V)-188                                                                            H                CH.sub.3       OCH.sub.3       OCH.sub.3                  (V)-189                                                                            H                CH.sub.3       H                                                                                               ##STR1639##               (V)-190                                                                            H                CH.sub.3       OCH.sub.3       CH.sub.3                   (V)-191                                                                            H                H              H               H                          (V)-192                                                                            H                H              H               H                          (V)-193                                                                            H                H              H               H                          (V)-194                                                                            CH.sub.3         CH.sub.2 OC.sub.2 H.sub.5                                                                     CH.sub.3        CH.sub.3                   (V)-195                                                                            H                C.sub.2 H.sub.5                                                                               H               H                          (V)-196                                                                            H                                                                                                ##STR1640##   CH.sub.3        CH.sub.3                   (V)-197                                                                            H                CH.sub.3       CH.sub.3        C.sub.2 H.sub.5            (V)-198                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-199                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-200                                                                            H                H              H               H                          (V)-201                                                                            H                H              H               H                          (V)-202                                                                            H                H              H               H                          (V)-203                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-204                                                                            H                H              H               H                          (V)-205                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-206                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-207                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   (V)-208                                                                            H                H              H               H                          (V)-209                                                                            H                CH.sub.3       CH.sub.3        CH.sub.3                   __________________________________________________________________________

                                      TABLE 41                                     __________________________________________________________________________     Com-                                                                           pound                                                                          No.  R.sup.1         R.sup.2                                                                             R.sup.3   R.sup.4                                                                               R.sup.5                                                                               R.sup.6                                                                              R.sup.7                __________________________________________________________________________     (VI)-1                                                                              OCH.sub.3       CH.sub.3                                                                             ##STR1641##                                                                             H      OCH.sub.3                                                                             CH.sub.3                                                                             H                      (VI)-2                                                                              CH(OCH.sub.3).sub.2                                                                            CH.sub.3                                                                             ##STR1642##                                                                             H      CH.sub.3                                                                              CH.sub.3                                                                             CH.sub.3               (VI)-3                                                                              CH(OCH.sub.3).sub.2                                                                            H    H         H      CH.sub.3                                                                              CH.sub.3                                                                             CH.sub.3               (VI)-4                                                                              CH.sub.3        CH.sub.3                                                                            H         H      H      H     H                      (VI)-5                                                                               ##STR1643##    CH.sub.3                                                                            H         H      H      H     H                      (VI)-6                                                                               ##STR1644##    CH.sub.3                                                                            H         H      H      CH.sub.3                                                                             H                      (VI)-7                                                                              CH.sub.3        CH.sub.3                                                                            H         H      H      OCH.sub.3                                                                            H                      (VI)-8                                                                              CH.sub.3        CH.sub.3                                                                            H         H      CH.sub.2 OCH.sub.3                                                                    CH.sub.3                                                                             CH.sub.3               (VI)-9                                                                               ##STR1645##    CH.sub.3                                                                            H         H      H      H     H                      (VI)-10                                                                             CH.sub.3        CH.sub.3                                                                            H         H      CH.sub.3                                                                              CH.sub.3                                                                             CH.sub.3               (VI)-11                                                                             H               H                                                                                    ##STR1646##                                                                             H      H      H     H                      (VI)-12                                                                              ##STR1647##    CH.sub.3                                                                            H         H      CH.sub.3                                                                              CH.sub.3                                                                             CH.sub.3               (VI)-13                                                                             H               H    H         H      CH.sub.3                                                                              CH.sub.3                                                                             CH.sub.3               (VI)-14                                                                             H               H    H                                                                                         ##STR1648##                                                                          H      OCH.sub.3                                                                            OCH.sub.3              (VI)-15                                                                              ##STR1649##    H    H         H      H      OCH.sub.3                                                                            H                      (VI)-16                                                                             CH.sub.3        CH.sub.3                                                                            H         H      OCH.sub.3                                                                             H     CH.sub.3               (VI)-17                                                                              ##STR1650##    H    H         H      H      OCH.sub.3                                                                            H                      (VI)-18                                                                             H               H    H                                                                                         ##STR1651##                                                                          H      OCH.sub.3                                                                            H                      (VI)-19                                                                              ##STR1652##    CH.sub.3                                                                            H         H      CH.sub.3                                                                              CH.sub.3                                                                             CH.sub.3               (VI)-20                                                                              ##STR1653##    CH.sub.3                                                                            H         H      CH.sub.3                                                                              CH.sub.3                                                                             CH.sub.3               (VI)-21                                                                             CH.sub.3        CH.sub.3                                                                            H         H      H      H     CH.sub.3               (VI)-22                                                                              ##STR1654##    CH.sub.3                                                                            H         H      CH.sub.3                                                                              H     CH.sub.3               (VI)-23                                                                              ##STR1655##    CH.sub.3                                                                            H         H      CH.sub.3                                                                              OCH.sub.3                                                                            OCH.sub.3              (VI)-24                                                                              ##STR1656##    CH.sub.3                                                                            H         H      CH.sub.3                                                                              OCH.sub.3                                                                            OCH.sub.3              (VI)-25                                                                             H               H    H                                                                                         ##STR1657##                                                                          H      OCH.sub.3                                                                            OCH.sub.3              (VI)-26                                                                              ##STR1658##    CH.sub.3                                                                            H         H      CH.sub.3                                                                              H                                                                                     ##STR1659##           (VI)-27                                                                              ##STR1660##    OC.sub.2 H.sub.5                                                                    OCH.sub.3 H      H      H     H                      (VI)-28                                                                              ##STR1661##    OCH.sub.3                                                 OC.sub.2 H.sub.5                                                                    H               H    H         H                                          (VI)-29                                                                              ##STR1662##    CH.sub.3                                                                            H         H      H      H     CH.sub.3               (VI)-30                                                                              ##STR1663##    H                                                                                    ##STR1664##                                                                             H      H      H     H                      (VI)-31                                                                             CH.sub.3        H    H         H      CH.sub.3                                                                              CH.sub.3                                                                             CH.sub.3               (VI)-32                                                                              ##STR1665##    CH.sub.3                                                                            H         H      CH.sub.3                                                                              H     CH.sub.3               (VI)-33                                                                              ##STR1666##    CH.sub.3                                                                            H         H      H      CH.sub.3                                                                             CH.sub.3               (VI)-34                                                                             CH.sub.3        CH.sub.3                                                                            H         H      H      C.sub.4 H.sub.9                                                                      Ht)                    (VI)-35                                                                              ##STR1667##                                                              (VI)-36                                                                              ##STR1668##                                                              (VI)-37                                                                              ##STR1669##                                                              __________________________________________________________________________

    TABLE 42       - Compound       No. R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 R.sup.6 R.sup.7       (VII)-1 NH       ##STR1670##       CH.sub.3 H H H      (VII)-2 H H H H H       ##STR1671##       H      (VII)-3 H H H H H       ##STR1672##       H      (VII)-4 H H H H H H H       (VII)-5 CH.sub.3 CH.sub.3 H H H H H      (VII)-6       ##STR1673##       H CH.sub.3 CH.sub.3 H H H      (VII)-7       ##STR1674##       H CH.sub.3 CH.sub.3 H       ##STR1675##       H      (VII)-8 H H H H H       ##STR1676##       H      (VII)-9 H H H H H       ##STR1677##       H      (VII)-10 H H H H H       ##STR1678##       H      (VII)-11       ##STR1679##       H H H H H H      (VII)-12 NH       ##STR1680##       H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-13 CH.sub.3 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-14 H H       ##STR1681##       H H H H      (VII)-15 H H H H H       ##STR1682##       H      (VII)-16 H H H H H       ##STR1683##       H      (VII)-17 H H H H H       ##STR1684##       H      (VII)-18 CH.sub.3 CH.sub.3 H H H CH.sub.3 CH.sub.3       (VII)-19 CH.sub.3 H H H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-20       ##STR1685##       CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3       (VII)-21 H H H H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-22 NH  CH.sub.3       ##STR1686##       H C.sub.3 H.sub.7       (n) H                        (VII)-23 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 Br H H      CH.sub.3 CH.sub.3      (VII)-24       ##STR1687##       H C.sub.4 H.sub.9 (n) C.sub.2 H.sub.5 H C.sub.4 H.sub.9       (n) H                                                              (VII)-25       ##STR1688##       H C.sub.4 H.sub.9 (n) C.sub.2       H.sub.5 H      ##STR1689##       H      (VII)-26       ##STR1690##       H C.sub.4 H.sub.9 (n) C.sub.4 H.sub.9 (n) H C.sub.4 H.sub.9 (n) H      (VII)-27 OC.sub.2 H.sub.5 OC.sub.2       H.sub.5 H H H H H                      (VII)-28 OC.sub.2 H.sub.5      OC.sub.2       H.sub.5 H H H CH.sub.3 CH.sub.3      (VII)-29 CH.sub.3 H H H CH.sub.3 H H       (VII)-30 CH.sub.3 H H H H CH.sub.3 H       (VII)-31 H H CH.sub.3 CH.sub.3 H H H      (VII)-32       ##STR1691##       H CH.sub.3 CH.sub.3 H       ##STR1692##       H      (VII)-33       ##STR1693##       H CH.sub.3 H H OCH.sub.3 H      (VII)-34 H H H H H CH.sub.3 H      (VII)-35       ##STR1694##       ##STR1695##       ##STR1696##       H H H      (VII)-36 CH.sub.3 CH.sub.3 H H H H C.sub.4       H.sub.9                                                (VII)-37       ##STR1697##       H CH.sub.3 CH.sub.3 H C.sub.4 H.sub.9       (t) H                                            (VII)-38       ##STR1698##       H CH.sub.3 CH.sub.3 H C.sub.4 H.sub.9       (t) H                                            (VII)-39 OC.sub.8 H.sub.17 H      CH.sub.3 CH.sub.3 H C.sub.4 H.sub.9       (t) H                                         (VII)-40       ##STR1699##       H CH.sub.3 CH.sub.3 OC.sub.2 H.sub.5 H C.sub.4 H.sub.9       (t)                                                             (VII)-41 OC.sub.2      H.sub.5 H CH.sub.3 CH.sub.3 H H H      (VII)-42       ##STR1700##       ##STR1701##       C.sub.2       H.sub.5 H H H H             (VII)-43       ##STR1702##       H CH.sub.3 CH.sub.3 H H H      (VII)-44       ##STR1703##       H CH.sub.3 CH.sub.3 H H H      (VII)-45       ##STR1704##       H CH.sub.3 CH.sub.3 H H H      (VII)-46       ##STR1705##       H CH.sub.3 CH.sub.3 H       ##STR1706##       H      (VII)-47       ##STR1707##       H CH.sub.3 CH.sub.3 H H H      (VII)-48       ##STR1708##       H CH.sub.3 CH.sub.3 H H H      (VII)-49       ##STR1709##       H CH.sub.3 CH.sub.3 H H H      (VII)-50       ##STR1710##       H CH.sub.3 CH.sub.3 H H H      (VII)-51       ##STR1711##       H CH.sub.3 CH.sub.3 H H H      (VII)-52  OCHCHCH.sub.3 H CH.sub.3 CH.sub.3 H H H       (VII)-53 OCH.sub.2 CH.sub.2       CH.sub.3 H CH.sub.3 CH.sub.3 H H H                                  (VII)-54       ##STR1712##       H CH.sub.3 CH.sub.3 H H H      (VII)-55       ##STR1713##       H CH.sub.3 CH.sub.3 H H H      (VII)-56       ##STR1714##       ##STR1715##       H H H H H      (VII)-57       ##STR1716##       H CH.sub.3 H H OCH.sub.3 H      (VII)-58 OCH.sub.3 H CH.sub.3 CH.sub.3 H H H      (VII)-59       ##STR1717##       H CH.sub.3 CH.sub.3 H OCH.sub.3 H      (VII)-60       ##STR1718##       H CH.sub.3 CH.sub.3 H H H      (VII)-61 CH.sub.3 H       ##STR1719##       H H OCH.sub.3 H      (VII)-62       ##STR1720##       H H H H H H      (VII)-63       ##STR1721##       H CH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3      (VII)-64       ##STR1722##       H CH.sub.3 CH.sub.3 H CH.sub.3 H      (VII)-65       ##STR1723##       H CH.sub.3 CH.sub.3 H H H      (VII)-66 CH.sub.3 CH.sub.3       ##STR1724##       H H H H      (VII)-67       ##STR1725##       H CH.sub.3 CH.sub.3 H C.sub.4 H.sub.9       (t) H                                            (VII)-68       ##STR1726##       H CH.sub.3 CH.sub.3 H H H      (VII)-69       ##STR1727##       H CH.sub.3 CH.sub.3 H H H      (VII)-70 OC.sub.2       H.sub.5 CH.sub.3 CH.sub.3 H H H H                       (VII)-71 OC.sub.2 H.sub.5 H CH.sub.3 CH.sub.3 H      CH.sub.3 CH.sub.3      (VII)-72       ##STR1728##       H CH.sub.3 H H H H      (VII)-73       ##STR1729##       H CH.sub.3 H H H H      (VII)-74       ##STR1730##       H CH.sub.3 H H H H      (VII)-75       ##STR1731##       H  H H H H      (VII)-76 OCH.sub.2       CHCH.sub.2 H CH.sub.3 CH.sub.3 H H H                        (VII)-77       ##STR1732##       H CH.sub.3 CH.sub.3 CH.sub.3 OC.sub.4 H.sub.9       (t) H                                                    (VII)-78 OC.sub.4 H.sub.9      (n) H CH.sub.3 CH.sub.3 H H H      (VII)-79 CH.sub.3 CH.sub.3 H H H OC.sub.4 H.sub.9       (t) H                                                       (VII)-80 CH.sub.3      CH.sub.3 H H H H C.sub.4       H.sub.9                              (VII)-81       ##STR1733##       H CH.sub.3 CH.sub.3 H OC.sub.4 H.sub.9       (t) H                                             (VII)-82       ##STR1734##       H CH.sub.3 CH.sub.3 H OC.sub.4 H.sub.9       (t) H                                             (VII)-83       ##STR1735##       H CH.sub.3 CH.sub.3 H OC.sub.4 H.sub.9       (t) H                                             (VII)-84 OC.sub.2 H.sub.5 H      CH.sub.3 CH.sub.3 H OC.sub.4 H.sub.9       (t) H                                (VII)-85 OC.sub.2 H.sub.5 H      CH.sub.3 CH.sub.3 H H C.sub.4       H.sub.9                                     (VII)-86 N(CH.sub.3).sub.2      H CH.sub.3 CH.sub.3 H H H      (VII)-87       ##STR1736##       H CH.sub.3 CH.sub.3 H       ##STR1737##       H      (VII)-88       ##STR1738##       H CH.sub.3 CH.sub.3 H       ##STR1739##       H      (VII)-89       ##STR1740##       H CH.sub.3 CH.sub.3 H H       ##STR1741##      (VII)-90       ##STR1742##       H CH.sub.3 CH.sub.3 H H H      (VII)-91 OC.sub.3 H.sub.7       (iso) H CH.sub.3 CH.sub.3 H H H                               (VII)-92       ##STR1743##       H CH.sub.3 CH.sub.3 H C.sub.3 H.sub.7       (iso) H                                            (VII)-93       ##STR1744##       H OC.sub.3 H.sub.7       (iso) H H H H                         (VII)-94       ##STR1745##       H H H H CH.sub.3 CH.sub.3      (VII)-95       ##STR1746##       H CH.sub.3 H H H       ##STR1747##      (VII)-96 CH.sub.3 CH.sub.3 H H CH.sub.3 H CH.sub.3       (VII)-97 H H CH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3       (VII)-98 N(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 H H H       (VII)-99 OC.sub.2 H.sub.5 H CH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3             (VII)-100 OC.sub.2 H.sub.5 H CH.sub.3 CH.sub.3 H CH.sub.3 H             (VII)-101 OC.sub.2 H.sub.5 H CH.sub.3 CH.sub.3 H H CH.sub.3             (VII)-102 CH.sub.3 H H H H H H       (VII)-103 H H H H H CH.sub.3 H       (VII)-104 CH.sub.3 CH.sub.3 CH.sub.3 H H H H       (VII)-105 CH.sub.3 H H H CH.sub.3 H CH.sub.3       (VII)-106 C.sub.2       H.sub.5 H H H CH.sub.3 CH.sub.3 CH.sub.3               (VII)-107      CH.sub.3 H CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.3       (VII)-108 CH.sub.3 H C.sub.2       H.sub.5 H H H H                                   (VII)-109       ##STR1748##       H H H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-110       ##STR1749##       H CH.sub.3 H H H H      (VII)-111 CH.sub.3 CH.sub.3 CH.sub.3 H H C.sub.3 H.sub.7       (n) H            (VII)-112 C.sub.3 H.sub.7 H H H CH.sub.3 CH.sub.3      CH.sub.3      (VII)-113       ##STR1750##       H H H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-114       ##STR1751##       H CH.sub.3 H H H H      (VII)-115       ##STR1752##       H CH.sub.3 H H H H      (VII)-116       ##STR1753##       H H H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-117 H H CH.sub.3 H H CH.sub.3 H      (VII)-118       ##STR1754##       H CH.sub.3 H H H H      (VII)-119       ##STR1755##       CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-120       ##STR1756##       H H H H OCH.sub.3 H      (VII)-121       ##STR1757##       CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-122       ##STR1758##       H H H H H H      (VII)-123       ##STR1759##       H H H H H H      (VII)-124 H H CH.sub.3 H OCH.sub.3 H H      (VII)-125       ##STR1760##       H CH.sub.3 H H H H      (VII)-126       ##STR1761##       H H H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-127 CH.sub.3 CH.sub.3       ##STR1762##       H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-128       ##STR1763##       CH.sub.3 H H H OCH.sub.3 H      (VII)-129 CH.sub.3 CH.sub.3       ##STR1764##       H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-130 CH.sub.3 CH.sub.3       ##STR1765##       H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-131 CH.sub.3 CH.sub.3       ##STR1766##       H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-132       ##STR1767##       H CH.sub.3 H CH.sub.3 OCH.sub.3 H      (VII)-133       ##STR1768##       H H H CH.sub.3 OCH.sub.3 H      (VII)-134 CH.sub.3 CH.sub.3       ##STR1769##       H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-135 CH.sub.3 CH.sub.3       ##STR1770##       H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-136 CH.sub.3 CH.sub.3       ##STR1771##       H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-137 CH.sub.3 CH.sub.3       ##STR1772##       H H H H      (VII)-138 CH.sub.3 CH.sub.3       ##STR1773##       H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-139 CH.sub.3 CH.sub.3       ##STR1774##       H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-140 CH.sub.3 CH.sub.3       ##STR1775##       H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-141       ##STR1776##       H CH.sub.3 H H       ##STR1777##       H      (VII)-142 CH.sub.3 CH.sub.3       ##STR1778##       H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-143       ##STR1779##       CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-144       ##STR1780##       CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3      (VII)-145       ##STR1781##       CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3       (VII)-146       ##STR1782##      (VII)-147       ##STR1783##

                                      TABLE 43                                     __________________________________________________________________________     Compound                                                                       No.   R.sup.1            R.sup.2   R.sup.3        R.sup.4  R.sup.5             __________________________________________________________________________     (VIII)-1                                                                              ##STR1784##       H         Br             CH.sub.2 N(CH.sub.3).sub                                                       .2       H                   (VIII)-2                                                                              ##STR1785##       CH.sub.3  C.sub.3 H.sub.7 (n)                                                                           H        Cl                  (VIII)-3                                                                             H                  H         H              H        H                   (VIII)-4                                                                              ##STR1786##       H         H              OCH.sub.3                                                                               H                   (VIII)-5                                                                             H                  H         H              CH.sub.3 CH.sub.3            (VIII)-6                                                                              ##STR1787##       H         CH.sub.3       CH.sub.3 H                   (VIII)-7                                                                             C.sub.2 H.sub.5    H         CH.sub.3       CH.sub.3 CH.sub.3            (VIII)-8                                                                              ##STR1788##       CH.sub.3  C.sub.3 H.sub.7 (n)                                                                           H        H                   (VIII)-9                                                                             C.sub.6 H.sub.13 (n)                                                                              H         H              H        H                   (VIII)-10                                                                             ##STR1789##       H         H              OCH.sub.3                                                                               H                   (VIII)-11                                                                             ##STR1790##       H         H              H        H                   (VIII)-12                                                                             ##STR1791##       CH.sub.3  H              H        H                   (VIII)-13                                                                             ##STR1792##       CH.sub.3  C.sub.3 H.sub.7 (n)                                                                           H        H                   (VIII)-14                                                                            CH.sub.3                                                                                           ##STR1793##                                                                             H              OCH.sub.3                                                                               H                   (VIII)-15                                                                             ##STR1794##       CH.sub.3  H              H        H                   (VIII)-16                                                                             ##STR1795##       CH.sub.3  C.sub.3 H.sub.7 (n)                                                                           H        H                   (VIII)-17                                                                            H                  CH.sub.3  H              H        H                   (VIII)-18                                                                             ##STR1796##       H         H              H        H                   (VIII)-19                                                                            H                  CH.sub.3  CH.sub.2 CHCH.sub.2                                                                           H        H                   (VIII)-20                                                                            H                  CH.sub.3  C.sub.3 H.sub.7 (n)                                                                           H        H                   (VIII)-21                                                                            CH.sub.3           CH.sub.3  CH.sub.3       CH.sub.3 CH.sub.3            (VIII)-22                                                                            H                                                                                                  ##STR1797##                                                                             H              H        H                   (VIII)-23                                                                            CH.sub.3           H         CH.sub.3       CH.sub.3 CH.sub.3            (VIII)-24                                                                             ##STR1798##       CH.sub.3  H              H        H                   (VIII)-25                                                                             ##STR1799##       CH.sub.3  H              H        H                   (VIII)-26                                                                            Br                                                                                                 ##STR1800##                                                                             CH.sub.2 N(CH.sub.3).sub.2                                                                    H        H                   (VIII)-27                                                                             ##STR1801##       CH.sub.3  H              H        H                   (VIII)-28                                                                             ##STR1802##       C.sub.4 H.sub.9 (n)                                                                      H              H        H                   (VIII)-29                                                                             ##STR1803##       C.sub.4 H.sub.9 (n)                                                                      H              H        H                   (VIII)-30                                                                             ##STR1804##       C.sub.2 H.sub.5                                                                          H              H        H                   (VIII)-31                                                                            CH.sub.3           CH.sub.3  H              H        H                   (VIII)-32                                                                             ##STR1805##       H         CH.sub.2 N(CH.sub.3).sub.2                                                                    H        H                   (VIII)-33                                                                            H                                                                                                  ##STR1806##                                                                             CH.sub.2 N(CH.sub.3).sub.2                                                                    H        H                   (VIII)-34                                                                             ##STR1807##                                                                                       ##STR1808##                                                                             CH.sub.2 N(CH.sub.3).sub.2                                                                    H        H                   (VIII)-35                                                                             ##STR1809##                                                                                       ##STR1810##                                                                             H                                                                                              ##STR1811##                                                                            H                   (VIII)-36                                                                             ##STR1812##       C.sub.2 H.sub.5                                                                          H              H        H                   (VIII)-37                                                                            C.sub.2 H.sub.5                                                                                    ##STR1813##                                                                             H              H        H                   (VIII)-38                                                                            C.sub.2 H.sub.5                                                                                    ##STR1814##                                                                             H              H        H                   (VIII)-39                                                                             ##STR1815##       C.sub.2 H.sub.5                                                                          H              H        H                   (VIII)-40                                                                             ##STR1816##       C.sub.2 H.sub.5                                                                          H              H        H                   (VIII)-41                                                                             ##STR1817##       C.sub.2 H.sub.5                                                                          H              H        H                   (VIII)-42                                                                             ##STR1818##       C.sub.2 H.sub.5                                                                          H              H        H                   (VIII)-43                                                                             ##STR1819##       CH.sub.3  H              H        H                   (VIII)-44                                                                             ##STR1820##       H         H              H        H                   (VIII)-45                                                                            CH.sub.3                                                                                           ##STR1821##                                                                             H              H        H                   (VIII)-46                                                                             ##STR1822##       C.sub.3 H.sub.7 (n)                                                                      H              H        H                   (VIII)-47                                                                             ##STR1823##                                                                                       ##STR1824##                                                                             H              OCH.sub.3                                                                               H                   (VIII)-48                                                                             ##STR1825##       CH.sub.3  H              OCH.sub.3                                                                               H                   (VIII)-49                                                                             ##STR1826##                                                                                       ##STR1827##                                                                             H              OCH.sub.3                                                                               H                   (VIII)-50                                                                             ##STR1828##       H         H              H        H                   (VIII)-51                                                                             ##STR1829##                                                                                       ##STR1830##                                                                             H                                                                                              ##STR1831##                                                                            H                   (VIII)-52                                                                             ##STR1832##                                                                                       ##STR1833##                                                                             H                                                                                              ##STR1834##                                                                            H                   (VIII)-53                                                                             ##STR1835##       CH.sub.3  H              H        H                   (VIII)-54                                                                             ##STR1836##       CH.sub.3  H              H        H                   (VIII)-55                                                                             ##STR1837##       C.sub.3 H.sub.7                                                                          H              H        H                   (VIII)-56                                                                            CH.sub.3           H         H              H        H                   (VIII)-57                                                                             ##STR1838##                                                                                       ##STR1839##                                                                             H              H        H                   (VIII)-58                                                                             ##STR1840##       CH.sub.3  H              H        H                   (VIII)-59                                                                             ##STR1841##       CH.sub.3  H              H        H                   (VIII)-60                                                                             ##STR1842##       CH.sub.3  H              H        H                   (VIII)-61                                                                            CH.sub.3                                                                                           ##STR1843##                                                                             H              H        H                   (VIII)-62                                                                             ##STR1844##       CH.sub.3  H              H        H                   (VIII)-63                                                                             ##STR1845##       CH.sub.3  H              H        H                   (VIII)-64                                                                            CH.sub.3                                                                                           ##STR1846##                                                                             H              H        H                   (VIII)-65                                                                             ##STR1847##       CH.sub.3  H              H        H                   (VIII)-66                                                                             ##STR1848##       CH.sub.3  H              H        H                   (VIII)-67                                                                             ##STR1849##       CH.sub.3  H              H        H                   (VIII)-68                                                                            CHCHCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           H         H              H        H                   (VIII)-69                                                                             ##STR1850##       H         H              H        H                   (VIII)-70                                                                             ##STR1851##                                                                                       ##STR1852##                                                                             H                                                                                              ##STR1853##                                                                            H                   (VIII)-71                                                                             ##STR1854##       C.sub.3 H.sub.7 (n)                                                                      H              H        H                   (VIII)-72                                                                            C.sub.3 H.sub.7 (n)                                                                                ##STR1855##                                                                             H              H        H                   (VIII)-73                                                                             ##STR1856##                                                                                       ##STR1857##                                                                             H              H        H                   (VIII)-74                                                                             ##STR1858##       C.sub.3 H.sub.7 (n)                                                                      H              H        H                   (VIII)-75                                                                            C.sub.3 H.sub.7 (n)                                                                                ##STR1859##                                                                             H              H        H                   (VIII)-76                                                                             ##STR1860##       C.sub.14 H.sub.29 (n)                                                                    H              H        H                   (VIII)-77                                                                             ##STR1861##       C.sub.3 H.sub.7 (n)                                                                      H              H        H                   (VIII)-78                                                                            H                  CH.sub.2 CH.sub.2 NH.sub.2 (n)                                                           H              H        H                   (VIII)-79                                                                             ##STR1862##                                                                                       ##STR1863##                                                                             CH.sub.2 N(CH.sub.3).sub.2                                                                    H        H                   (VIII)-80                                                                            H                  CH.sub.3  H              CH.sub.3 H                   (VIII)-81                                                                             ##STR1864##                                                                                       ##STR1865##                                                                             H              H        H                   (VIII)-82                                                                             ##STR1866##                                                                                       ##STR1867##                                                                              ##STR1868##   H        H                   (VIII)-83                                                                             ##STR1869##                                                                                       ##STR1870##                                                                              ##STR1871##   H        H                   (VIII)-84                                                                             ##STR1872##                                                                                       ##STR1873##                                                                              ##STR1874##   H        H                   (VIII)-85                                                                            C.sub.2 H.sub.5    H         H              H        H                   (VIII)-86                                                                            CH.sub.3           CH.sub.3  H              C.sub.2 H.sub.5                                                                         H                   (VIII)-87                                                                             ##STR1875##       H         H              H        H                   (VIII)-88                                                                             ##STR1876##                                                                                       ##STR1877##                                                                              ##STR1878##   H        H                   (VIII)-89                                                                             ##STR1879##                                                                                       ##STR1880##                                                                              ##STR1881##   H        H                   (VIII)-90                                                                             ##STR1882##                                                                                       ##STR1883##                                                                              ##STR1884##   H        H                   (VIII)-91                                                                            CH.sub.3           H         H              CH.sub.3 H                   (VIII)-92                                                                             ##STR1885##       C.sub.4 H.sub.9 (Sn)                                                                     H              H        H                   (VIII)-93                                                                            C.sub.2 H.sub.5    CH.sub.3  H              H        H                   (VIII)-94                                                                            C.sub.3 H.sub.7 (n)                                                                               C.sub.2 H.sub.5                                                                          H              H        H                   (VIII)-95                                                                            C.sub.5 H.sub.11 (n)                                                                              CH.sub.3  H              H        H                   (VIII)-96                                                                             ##STR1886##                 CH.sub.3       CH.sub.3 CH.sub.3            (VIII)-97                                                                            H                  CH.sub.3  OCH.sub.3      H        H                   (VIII)-98                                                                             ##STR1887##       H         H              H        H                   (VIII)-99                                                                             ##STR1888##       H         CH.sub.3       CH.sub.3 H                   (VIII)-100                                                                            ##STR1889##                                H        H                   __________________________________________________________________________

                  TABLE 44                                                         ______________________________________                                          ##STR1890##                 (IX)-1                                             ##STR1891##                 (IX)-2                                             ##STR1892##                 (IX)-3                                             ##STR1893##                 (IX)-4                                             ##STR1894##                 (IX)-5                                             ##STR1895##                 (IX)-6                                             ##STR1896##                 (IX)-7                                             ##STR1897##                 (IX)-8                                             ##STR1898##                 (IX)-9                                             ##STR1899##                 (IX)-10                                           ______________________________________                                    

                  TABLE 45                                                         ______________________________________                                          ##STR1900##                 (X)-1                                              ##STR1901##                 (X)-2                                              ##STR1902##                 (X)-3                                              ##STR1903##                 (X)-4                                              ##STR1904##                 (X)-5                                              ##STR1905##                 (X)-6                                              ##STR1906##                 (X)-7                                              ##STR1907##                 (X)-8                                              ##STR1908##                 (X)-9                                              ##STR1909##                 (X)-10                                             ##STR1910##                 (X)-11                                             ##STR1911##                 (X)-12                                             ##STR1912##                 (X)-13                                             ##STR1913##                 (X)-14                                             ##STR1914##                 (X)-15                                             ##STR1915##                 (X)-16                                             ##STR1916##                 (X)-17                                             ##STR1917##                 (X)-18                                             ##STR1918##                 (X)-19                                             ##STR1919##                 (X)-20                                             ##STR1920##                 (X)-21                                             ##STR1921##                 (X)-22                                             ##STR1922##                 (X)-23                                             ##STR1923##                 (X)-24                                             ##STR1924##                 (X)-25                                             ##STR1925##                 (X)-26                                             ##STR1926##                 (X)-27                                            ______________________________________                                    

                  TABLE 46                                                         ______________________________________                                          ##STR1927##                 (XI)-1                                             ##STR1928##                 (XI)-2                                             ##STR1929##                 (XI)-3                                             ##STR1930##                 (XI)-4                                             ##STR1931##                 (XI)-5                                             ##STR1932##                 (XI)-6                                             ##STR1933##                 (XI)-7                                             ##STR1934##                 (XI)-8                                             ##STR1935##                 (XI)-9                                             ##STR1936##                 (XI)-10                                            ##STR1937##                 (XI)-11                                            ##STR1938##                 (XI)-12                                            ##STR1939##                 (XI)-13                                            ##STR1940##                 (XI)-14                                            ##STR1941##                 (XI)-15                                            ##STR1942##                 (XI)-16                                            ##STR1943##                 (XI)-17                                            ##STR1944##                 (XI)-18                                            ##STR1945##                 (XI)-19                                            ##STR1946##                 (XI)-20                                            ##STR1947##                 (XI)-21                                            ##STR1948##                 (XI)-22                                            ##STR1949##                 (XI)-23                                            ##STR1950##                 (XI)-24                                            ##STR1951##                 (XI)-25                                            ##STR1952##                 (XI)-26                                            ##STR1953##                 (XI)-27                                            ##STR1954##                 (XI)-28                                            ##STR1955##                 (XI)-29                                           ______________________________________                                    

                  TABLE 47                                                         ______________________________________                                          ##STR1956##                (XII)-1                                             ##STR1957##                (XII)-2                                             ##STR1958##                (XII)-3                                             ##STR1959##                (XII)-4                                             ##STR1960##                (XII)-5                                             ##STR1961##                (XII)-6                                             ##STR1962##                (XII)-7                                             ##STR1963##                (XII)-8                                             ##STR1964##                (XII)-9                                             ##STR1965##                (XII)-10                                            ##STR1966##                (XII)-11                                            ##STR1967##                (XII)-12                                            ##STR1968##                (XII)-13                                            ##STR1969##                (XII)-14                                            ##STR1970##                (XII)-15                                            ##STR1971##                (XII)-16                                            ##STR1972##                (XII)-17                                            ##STR1973##                (XXI)-18                                            ##STR1974##                (XII)-19                                            ##STR1975##                (XII)-20                                            ##STR1976##                (XII)-21                                            ##STR1977##                (XII)-22                                            ##STR1978##                (XII)-23                                            ##STR1979##                (XII)-24                                            ##STR1980##                (XII)-25                                            ##STR1981##                (XII)-26                                            ##STR1982##                (XII)-27                                            ##STR1983##                (XII)-28                                            ##STR1984##                (XII)-29                                            ##STR1985##                (XII)-30                                            ##STR1986##                (XII)-31                                            ##STR1987##                (XII)-32                                            ##STR1988##                (XII)-33                                            ##STR1989##                (XII)-34                                            ##STR1990##                (XII)-35                                            ##STR1991##                (XII)-36                                            ##STR1992##                (XII)-37                                            ##STR1993##                (XII)-38                                            ##STR1994##                (XII)-39                                            ##STR1995##                (XII)-40                                            ##STR1996##                (XII)-41                                            ##STR1997##                (XII)-42                                            ##STR1998##                (XII)-43                                            ##STR1999##                (XII)-44                                            ##STR2000##                (XII)-45                                            ##STR2001##                (XII)-46                                            ##STR2002##                (XII)-47                                            ##STR2003##                (XII)-48                                            ##STR2004##                (XII)-49                                            ##STR2005##                (XII)-50                                            ##STR2006##                (XII)-51                                            ##STR2007##                (XII)-52                                            ##STR2008##                (XII)-53                                            ##STR2009##                (XII)-54                                            ##STR2010##                (XII)-55                                            ##STR2011##                (XII)-56                                            ##STR2012##                (XII)-57                                            ##STR2013##                (XII)-58                                            ##STR2014##                (XII)-59                                            ##STR2015##                (XII)-60                                            ##STR2016##                (XII)-61                                           ______________________________________                                    

FIGS. 1 to 4 are schematic cross-sectional views which show the embodiments of the electrophotographic photoconductor according to the present invention. Reference numeral 1 indicate an electroconductive support; and reference numeral 2, a single-layered photoconductive layer. Any embodiment is adoptable as long as the single-layered photoconductive layer 2 is formed on the electroconductive support 1. For instance, an undercoat layer 3 may be interposed between the electroconductive support 1 and the single-layered photoconductive layer 2 to improve the adhesion properties and the electric charge blocking characteristics, as shown in FIG. 2. In addition, a protective layer 4 may be formed on the single-layered photoconductive layer 2 to increase the mechanical durability such as the wear resistance of the photoconductor, as shown in FIG. 3. As shown in FIG. 4, both an undercoat layer 3 and a protective layer 4 may be provided.

For the electroconductive support for use in the photoconductor of the present invention, metals such as aluminum, brass, stainless steel and nickel, and alloys thereof can be employed. In addition, a thin film of electroconductive materials such as aluminum, silver, gold, nickel, indium oxide, and tin oxide may be formed on an electrically insulating support made of a material such as polyethylene terephthalate, polypropylene, nylon, glass and paper. Further, electroconductive particles such as carbon black, indium oxide and tin oxide may be dispersed in an appropriate resin, and the thus obtained resin may be provided on the above-mentioned electrically insulating support, and a sheet of may be treated to be electroconductive for the support. The shape of the electroconductive support is not limited, and a sheet-, drum- or belt-shaped support may be employed as occasion demands.

Any conventional binder resins can be employed in the single-layered photoconductive layer for use in the present invention. In particular, polymers with high electrically insulating properties and film-forming properties are preferable. For example, thermoplastic resins and thermosetting resins such as polystyrene, styrene--acrylonitrile copolymer, styrene--butadiene copolymer, styrene--maleic anhydride copolymer, polyester, polyvinyl chloride, vinyl chloride--vinyl acetate copolymer, polyvinyl acetate, polyvinylidene chloride, polyarylate resin, polycarbonate (bisphenol A and bisphenol Z), cellulose acetate resin, ethyl cellulose resin, polyvinyl butyral, polyvinyl formal, polyvinyltoluene, poly-N-vinylcarbazole, acrylic resin, silicone resin, epoxy resin, melamine resin, urethane resin, phenolic resin, and alkyd resin can be employed.

To prepare the electrophotographic photoconductor of the present invention, the previously mentioned disazo pigment and trisazo pigment are mixed and simultaneously pulverized. In this case, ketones, esters, alcohols, cyclic ethers and cyclic ketones may be used as the dispersing solvents. Of these solvents, cyclic ethers and cyclic ketones are preferable, and tetrahydrofuran and cyclohexanone are in particular preferably employed as the dispersing solvents from the viewpoint of the sensitizing effect of the azo pigments. Then, the charge transporting material and the binder resin are added to the above prepared mixture of azo pigments, and the thus obtained mixture is coated on the electroconductive support by dip coating, spray coating or bead coating. Thus, an electrophotographic photoconductor according to the present invention is prepared.

It is preferable that the amount of the simultaneously pulverized mixture of the above-mentioned azo pigments be in a range of 0.01 to 10 parts by weight to 10 parts by weight of the binder resin. When the mixture of the azo pigments is contained in such an amount, the residual potential can be decreased, and the decrease of the charging characteristics and mechanical strength can be prevented.

When the charge transporting material for use in the photoconductor of the present invention is an organic positive hole transporting material, it is preferable that the amount of the charge transporting material be in a range of 1 to 15 parts by weight to 10 parts by weight of the binder resin. When the charge transporting material is contained in the photoconductive layer in the above-mentioned amount, the photosensitivity can be increased and the decrease of the charging characteristics and the mechanical strength can be prevented.

When the charge transporting material comprises an organic positive hole transporting material and an organic acceptor compound, the amount of the organic acceptor compound is preferably in a range of 1 to 15 parts by weight to 10 parts by weight of the binder resin to prevent the deterioration of the charging characteristics during the repeated operations, and the deterioration of the photosensitivity and the mechanical strength.

The thickness of the single-layered photoconductive layer is preferably in the range of 5 to 100 μm, more preferably in the range of 10 to 50 μm when the increase of mechanical strength and decrease of the residual potential are taken into consideration.

Other features of this invention will become apparent in the course of the following description of exemplary embodiments, which are given for illustration of the invention and are not intended to be limiting thereof.

EXAMPLE I-1

An unsymmetrical disazo pigment of formula (1) in which R¹ and R² are hydrogen was prepared using the couplers No. 17 and No. 24 shown in TABLE 1. A trisazo pigment of formula (2) in which R³ is hydrogen was prepared using the coupler No. 70 shown in TABLE 2.

Five parts by weight of the disazo pigment and 5 parts by weight of the trisazo pigment were dispersed in a ball mill together with 70 parts by weight of methyl ethyl ketone for 5 days, and simultaneously pulverized.

The above prepared mixture was added to a solution consisting of 100 parts by weight of Z type polycarbonate with a molecular weight of 60,000, 300 parts by weight of tetrahydrofuran, 80 parts by weight of 4-diethylaminobenzaldehyde-1-benzyl-1-phenylhydrazone serving as the charge transporting material, and 0.1 parts by weight of a commercially available silicone oil (Trademark "KF-50", made by Shin-Etsu Chemical Co., Ltd.). Thus, a coating liquid for a photoconductive layer was obtained.

The thus obtained photoconductive layer coating liquid was coated on an aluminum plate (Trademark "A1080", made by Sumitomo Light Metal Industries, Ltd.) with a thickness of 0.2 mm by blade coating, dried at 150° C. for 20 minutes, so that a photoconductive layer with a thickness of 20 μm was formed on the electroconductive support.

Thus, an electrophotographic photoconductor No. I-1 according to the present invention was obtained.

The oxidation potential of the charge transporting material for use in Example I-1 was 0.50 V (vs SCE).

EXAMPLE I-2

The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the unsymmetrical disazo pigment for use in the photoconductive layer coating liquid in Example I-1 was replaced by a disazo pigment of formula (1) (R¹ =R² =hydrogen) which was prepared using the coupler No. 30 shown in TABLE 1.

Thus, an electrophotographic photoconductor No. I-2 according to the present invention was obtained.

EXAMPLE I-3

The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the trisazo pigment for use in the photoconductive layer coating liquid in Example I-1 was replaced by a trisazo pigment of formula (2) (R³ =hydrogen) which was prepared using the coupler No. 214 shown in TABLE 13.

Thus, an electrophotographic photoconductor No. I-3 according to the present invention was obtained.

EXAMPLE I-4

The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the unsymmetrical disazo pigment for use in the photoconductive layer coating liquid in Example I-1 was replaced by a symmetrical disazo pigment of formula (1) (R² =R² =hydrogen) which was prepared using the coupler No. 17 shown in TABLE 1.

Thus, an electrophotographic photoconductor No. I-4 according to the present invention was obtained.

EXAMPLE I-5

The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the trisazo pigment for use in the photoconductive layer coating liquid in Example I-1 was replaced by a trisazo pigment of formula (2) (R³ =hydrogen) which was prepared using the coupler No. 3 shown in TABLE 1.

Thus, an electrophotographic photoconductor No. I-5 according to the present invention was obtained.

EXAMPLE I-6

The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example I-1 were separately changed to 0.04 parts by weight.

Thus, an electrophotographic photoconductor No. I-6 according to the present invention was obtained.

EXAMPLE I-7

The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example I-1 were separately changed to 0.05 parts by weight.

Thus, an electrophotographic photoconductor No. I-7 according to the present invention was obtained.

EXAMPLE I-8

The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example I-1 were separately changed to 50 parts by weight.

Thus, an electrophotographic photoconductor No. I-8 according to the present invention was obtained.

EXAMPLE I-9

The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example I-1 were separately changed to 75 parts by weight.

Thus, an electrophotographic photoconductor No. I-9 according to the present invention was obtained.

EXAMPLE I-10

The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the amount of the charge transporting material for use in the photoconductive layer coating liquid in Example I-1 was changed to 5 parts by weight.

Thus, an electrophotographic photoconductor No. I-10 according to the present invention was obtained.

EXAMPLE I-11

The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the amount of the charge transporting material for use in the photoconductive layer coating liquid in Example I-1 was changed to 10 parts by weight.

Thus, an electrophotographic photoconductor No. I-11 according to the present invention was obtained.

EXAMPLE I-12

The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the amount of the charge transporting material for use in the photoconductive layer coating liquid in Example I-1 was changed to 150 parts by weight.

Thus, an electrophotographic photoconductor No. I-12 according to the present invention was obtained.

EXAMPLE I-13

The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the amount of the charge transporting material for use in the photoconductive layer coating liquid in Example I-1 was changed to 200 parts by weight.

Thus, an electrophotographic photoconductor No. I-13 according to the present invention was obtained.

EXAMPLE I-14

The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that methyl ethyl ketone used in dispersing the azo pigments in Example I-1 was replaced by 1,4-dioxane.

Thus, an electrophotographic photoconductor No. I-14 according to the present invention was obtained.

EXAMPLE I-15

The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that methyl ethyl ketone used in dispersing the azo pigments in Example I-1 was replaced by isophorone.

Thus, an electrophotographic photoconductor No. I-15 according to the present invention was obtained.

EXAMPLE I-16

The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that methyl ethyl ketone used in dispersing the azo pigments in Example I-1 was replaced by tetrahydrofuran.

Thus, an electrophotographic photoconductor No. I-16 according to the present invention was obtained.

EXAMPLE I-17

The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that methyl ethyl ketone used in dispersing the azo pigments in Example I-1 was replaced by cyclohexanone.

Thus, an electrophotographic photoconductor No. I-17 according to the present invention was obtained.

COMPARATIVE EXAMPLE I-1

An unsymmetrical disazo pigment of formula (1) in which R¹ and R² are hydrogen was prepared using the couplers No. 17 and No. 24 shown in TABLE 1.

Ten parts by weight of the disazo pigment were dispersed in a ball mill together with 70 parts by weight of methyl ethyl ketone for 5 days.

The above prepared dispersion of the disazo pigment was added to a solution consisting of 100 parts by weight of Z type polycarbonate with a molecular weight of 60,000, 300 parts by weight of tetrahydrofuran, 80 parts by weight of 4-diethylaminobenzaldehyde-1-benzyl-1-phenylhydrazone serving as the charge transporting material, and 0.1 parts by weight of a commercially available silicone oil (Trademark "KF-50", made by Shin-Etsu Chemical Co., Ltd.). Thus, a coating liquid for a photoconductive layer was obtained.

The thus obtained photoconductive layer coating liquid was coated on an aluminum plate (Trademark "A1080", made by Sumitomo Light Metal Industries, Ltd.) with a thickness of 0.2 mm by blade coating, dried at 150° C. for 20 minutes, so that a photoconductive layer with a thickness of 20 μm was formed on the electroconductive support.

Thus, a comparative electrophotographic photoconductor No. I-1 was obtained.

COMPARATIVE EXAMPLE I-2

A trisazo pigment of formula (2) in which R³ is hydrogen was prepared using the coupler No. 70 shown in TABLE 2.

Ten parts by weight of the trisazo pigment were dispersed in a ball mill together with 70 parts by weight of methyl ethyl ketone for 5 days.

The above prepared dispersion of the trisazo pigment was added to a solution consisting of 100 parts by weight of Z type polycarbonate with a molecular weight of 60,000, 300 parts by weight of tetrahydrofuran, 80 parts by weight of 4-diethylaminobenzaldehyde-1-benzyl-1-phenylhydrazone serving as the charge transporting material, and 0.1 parts by weight of a commercially available silicone oil (Trademark "KF-50", made by Shin-Etsu Chemical Co., Ltd.). Thus, a coating liquid for a photoconductive layer was obtained.

The thus obtained photoconductive layer coating liquid was coated on an aluminum plate (Trademark "A1080", made by Sumitomo Light Metal Industries, Ltd.) with a thickness of 0.2 mm by blade coating, dried at 150° C. for 20 minutes, so that a photoconductive layer with a thickness of 20 μm was formed on the electroconductive support.

Thus, a comparative electrophotographic photoconductor No. I-2 was obtained.

COMPARATIVE EXAMPLE I-3

An unsymmetrical disazo pigment of formula (1) in which R¹ and R² are hydrogen was prepared using the couplers No. 17 and No. 24 shown in TABLE 1. A trisazo pigment of formula (2) in which R³ is hydrogen was prepared using the coupler No. 70 shown in TABLE 2.

Five parts by weight of the disazo pigment and 5 parts by weight of the trisazo pigment were separately dispersed in a ball mill with 35 parts by weight of methyl ethyl ketone for 5 days. Then, the dispersion of the disazo pigment and the dispersion of the trisazo pigment were mixed.

The above prepared mixture was added to a solution consisting of 100 parts by weight of Z type polycarbonate with a molecular weight of 60,000, 300 parts by weight of tetrahydrofuran, 80 parts by weight of 4-diethylaminobenzaldehyde-1-benzyl-1-phenylhydrazone serving as the charge transporting material, and 0.1 parts by weight of a commercially available silicone oil (Trademark "KF-50", made by Shin-Etsu Chemical Co., Ltd.). Thus, a coating liquid for a photoconductive layer was obtained.

The thus obtained photoconductive layer coating liquid was coated on an aluminum plate (Trademark "A1080", made by Sumitomo Light Metal Industries, Ltd.) with a thickness of 0.2 mm by blade coating, dried at 150° C. for 20 minutes, so that a photoconductive layer with a thickness of 20 μm was formed on the electroconductive support.

Thus, a comparative electrophotographic photoconductor No. I-3 was obtained.

The dynamic electrostatic properties of each of the electrophotographic photoconductors No. I-1 to No. I-17 according to the present invention and the comparative electrophotographic photoconductors No. I-1 to No. I-3 were measured by using a commercially available test apparatus (Trademark "EPA-8100", made by Kawaguchi Electro Works Co., Ltd.) under the circumstances of 25° C. and 50% RH.

More specifically, each photoconductor was charged positively in the dark under application of +6 kV for 10 seconds. Then, each photoconductor was allowed to stand in the dark for 20 seconds without applying any charge thereto. After that, the photoconductor was illuminated by white light of a halogen lamp in such a manner that the illuminance on the illuminated surface of the photoconductor was 10 lux. Similarly, the photoconductor was illuminated by a 780 nm-monochromatic light in such a manner that the illuminance on the illuminated surface of the photoconductor was 10 μW/cm² after charging and dark decay.

The charging potential was expressed by a surface potential V₂ (V), which was obtained two seconds after the initiation of charging; the photosensitivity was expressed by an exposure E.sub. 1/2 (lux·sec) required to reduce the surface potential obtained just before the exposure by the application of the white light to 1/2 the surface potential, and an exposure E.sub. 1/2 (μJ/cm²) required to reduce the surface potential obtained just before the exposure by the application of the monochromatic light to 1/2 the surface potential; and the residual potential was expressed by a surface potential V₃₀ (V) separately obtained after the exposure for 30 seconds by use of the white light and the monochromatic light.

The results are shown in TABLE 48.

                                      TABLE 48                                     __________________________________________________________________________                               Charge                                                                         Trans-                                                              Azo        porting                                                             Pigments/                                                                            Charge                                                                              Material/        E.sub. 1/2                                                                           V.sub.30                      Disazo    Trisazo                                                                             Binder                                                                               Trans-                                                                              Binder  E.sub. 1/2                                                                          V.sub.30                                                                           (mono-                                                                               (mono-                                                                               Solvent for             Coupler   Coupler                                                                             Resin porting                                                                             Resin                                                                               V.sub.2                                                                           (white)                                                                             (white)                                                                            chomatic)                                                                            chromatic)                                                                           dispersing              No.       No.  Ratio Material                                                                            Ratio                                                                               V  lux · sec                                                                  V   μJ/cm.sup.2                                                                       V     pigments                __________________________________________________________________________     Ex. I-1                                                                             17, 24                                                                              70   1/10  *    8/10 620                                                                               0.80 35  0.35  30    Methyl ethyl                                                                   ketone                  Ex. I-2                                                                             30   70   1/10  *    8/10 680                                                                               0.93 30  0.40  30    Methyl ethyl                                                                   ketone                  Ex. I-3                                                                             17, 24                                                                              214  1/10  *    8/10 620                                                                               1.02 30  0.40  30    Methyl ethyl                                                                   ketone                  Ex. I-4                                                                             17   70   1/10  *    8/10 610                                                                               0.91 35  0.41  40    Methyl ethyl                                                                   ketone                  Ex. I-5                                                                             17, 24                                                                               3   1/10  *    8/10 650                                                                               1.31 50  0.78  120   Methyl ethyl                                                                   ketone                  Ex. I-6                                                                             17, 24                                                                              70   0.008/10                                                                             *    8/10 660                                                                               0.85 70  0.40  80    Methyl ethyl                                                                   ketone                  Ex. I-7                                                                             17, 24                                                                              70   0.01/10                                                                              *    8/10 630                                                                               0.81 50  0.37  40    Methyl ethyl                                                                   ketone                  Ex. I-8                                                                             17, 24                                                                              70   10/10 *    8/10 630                                                                               0.81 10  0.36  15    Methyl ethyl                                                                   ketone                  Ex. I-9                                                                             17, 24                                                                              70   15/10 *    8/10 500                                                                               0.83  5  0.35   5    Methyl ethyl                                                                   ketone                  Ex. I-10                                                                            17, 24                                                                              70   1/10  *    0.5/10                                                                              680                                                                               0.90 40  0.41  35    Methyl ethyl                                                                   ketone                  Ex. I-11                                                                            17, 24                                                                              70   1/10  *    1/10 620                                                                               0.83 35  0.35  30    Methyl ethyl                                                                   ketone                  Ex. I-12                                                                            17, 24                                                                              70   1/10  *    15/10                                                                               620                                                                               0.80 35  0.35  30    Methyl ethyl                                                                   ketone                  Ex. I-13                                                                            17, 24                                                                              70   1/10  *    20/10                                                                               510                                                                               0.80 30  0.31  30    Methyl ethyl                                                                   ketone                  Ex. I-14                                                                            17, 24                                                                              70   1/10  *    8/10 530                                                                               0.70 30  0.32  35    Dioxane                 Ex. I-15                                                                            17, 24                                                                              70   1/10  *    8/10 620                                                                               0.75 30  0.32  35    Isophorone              Ex. I-16                                                                            17, 24                                                                              70   1/10  *    8/10 620                                                                               0.52 30  0.28  30    Tetrahydro-                                                                    furan                   Ex. 1-17                                                                            17, 24                                                                              70   1/10  *    8/10 610                                                                               0.50 30  0.28  30    Cyclohexanone           Comp.                                                                               17, 24                                                                              --   1/10  *    8/10 610                                                                               1.10 35  3.00  40    Methyl ethyl            Ex. I-1                                                ketone                  Comp.                                                                               --   70   1/10  *    8/10 650                                                                               0.80 35  No    --    Methyl ethyl            Ex. I-2                                    sensitivity ketone                  Comp.                                                                               17, 24                                                                              70   1/10  *    8/10 620                                                                               1.50 40  1.32  40    Methyl ethyl            Ex. I-3                                                ketone                  __________________________________________________________________________      *4-diethylaminobenzaldehyde-1-benzyl-1-phenylhydrazone                   

EXAMPLES I-18 TO I-38

The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the charge transporting material, 4-diethylaminobenzaldehyde-1-benzyl-1-phenylhydrazone, used in the photoconductive layer coating liquid in Example I-1 was replaced by the respective charge transporting materials as shown in TABLE 49.

Thus, electrophotographic photoconductors No. I-18 to No. I-38 according to the present invention were obtained.

The oxidation potential of each charge transporting material is also shown in TABLE 49.

                  TABLE 49                                                         ______________________________________                                                                   Oxidation                                                                      Potential                                            Charge Transporting Material                                                                             [V (vs SCE)]                                         ______________________________________                                         Ex. I-18                                                                              9-ethylcarbazole-3-aldehyde-1-methyl-                                                                 0.74                                                    1-phenylhydrazone                                                       Ex. I-19                                                                              9-ethylcarbazole-3-aldehyde-1-benzyl-                                                                 0.81                                                    1-phenylhydrazone                                                       Ex. I-20                                                                              2-methoxynaphthalene-1-aldehyde-1-                                                                    0.79                                                    benzyl-1-phenylhydrazone                                                Ex. I-21                                                                              2,2'-dimethyl-4,4'-bis(diethylamino)-                                                                 0.66                                                    triphenylmethane                                                        Ex. I-22                                                                              9-(4-diethylaminostyryl)anthracene                                                                    0.52                                             Ex. I-23                                                                              3-(4-ethoxystyryl)-9-ethylcarbazole                                                                   0.76                                             Ex. I-24                                                                              4-diphenylaminostilbene                                                                               0.89                                             Ex. I-25                                                                              4'-diphenylamino-α-phenylstilbene                                                               0.86                                             Ex. I-26                                                                              4'-bis(4-methylphenyl)amino-α-phenyl-                                                           0.76                                                    stilbene                                                                Ex. I-27                                                                              4'-(4-methoxy)diphenylamino-α-phenyl-                                                           0.74                                                    stilbene                                                                Ex. I-28                                                                              N,N'-diphenyl-N,N'-bis(3-methyl-                                                                      0.73                                                    phenyl)-[1,1'-biphenyl]-4,4'-diamine                                    Ex. I-29                                                                              4'-methoxy-N,N'-bis(4-methylphenyl)-                                                                  0.76                                                    [1,1'-biphenyl]-4-amine                                                 Ex. I-30                                                                              N,N'-bis(4-methylphenyl)-[1,1'-                                                                       0.81                                                    biphenyl]-4-amine                                                       Ex. I-31                                                                              1-di(p-tolylamino)pyrene                                                                              0.81                                             Ex. I-32                                                                              1,4-bis[4-di(p-tolyl)aminostyryl]-                                                                    0.89                                                    benzene                                                                 Ex. I-33                                                                              4,4',4"-trimethoxytriphenylamine                                                                      0.52                                             Ex. I-34                                                                              4-methoxytriphenylamine                                                                               0.77                                             Ex. I-35                                                                              4,4'-dimethyltriphenylamine                                                                           0.84                                             Ex. I-36                                                                              N-ethyl-3,6-tetrabenzylaminocarbazole                                                                 0.31                                             Ex. I-37                                                                              1-phenyl-3-(4-diethylaminostyryl)-5-                                                                  0.47                                                    (4-diethylaminophenyl)pyrazoline                                        Ex. I-38                                                                              1,3-diphenyl-5-(4-dimethylamino-                                                                      0.67                                                    phenyl)pyrazoline                                                       ______________________________________                                    

The dynamic electrostatic properties of each of the electrophotographic photoconductors No. I-1 and Nos. I-18 to I-38 according to the present invention were measured by using a commercially available test apparatus (Trademark "EPA-8100", made by Kawaguchi Electro Works Co., Ltd.) under the circumstances of 25° C. and 50% RH.

More specifically, each photoconductor was charged positively in the dark under application of +6 kV for 10 seconds. Then, each photoconductor was allowed to stand in the dark for 20 seconds without applying any charge thereto. After that, the photoconductor was illuminated by white light of a halogen lamp in such a manner that the illuminance on the illuminated surface of the photoconductor was 10 lux.

The charging potential was expressed by a saturated surface potential Vm (V), which was obtained in the charging time of ten seconds; and the photosensitivity was expressed by an exposure E.sub. 1/2 (lux·sec) required to reduce the surface potential obtained just before the exposure to 1/2 the surface potential. The results are shown in TABLE 50.

Further, the saturated surface potential Vm (V) was plotted as a function of the oxidation potential of the charge transporting material as shown in FIG. 5.

                  TABLE 50                                                         ______________________________________                                                     Vm (V) E.sub. 1/2 (lux · sec)                             ______________________________________                                         Example I-1    700     0.80                                                    Example I-18  1070     0.83                                                    Example I-19  1290     0.75                                                    Example I-20  1400     1.02                                                    Example I-21  1080     0.88                                                    Example I-22   950     0.89                                                    Example I-23  1330     1.10                                                    Example I-24  1380     0.70                                                    Example I-25  1300     0.72                                                    Example I-26  1210     0.66                                                    Example I-27  1190     0.64                                                    Example I-28  1210     0.55                                                    Example I-29  1150     0.73                                                    Example I-30  1270     0.75                                                    Example I-31  1200     0.67                                                    Example I-32  1530     0.73                                                    Example I-33   300     1.48                                                    Example I-34  1320     1.38                                                    Example I-35  1450     4.00                                                    Example I-36   130     1.30                                                    Example I-37   330     1.20                                                    Example I-38  1350     1.46                                                    ______________________________________                                    

To evaluate the stability of the electrostatic properties of the photoconductor, using the electrophotographic photoconductors No. I-1, No. I-20 and No. I-28 according to the present invention, the saturated surface potential Vm (V) and the exposure E.sub. 1/2 (lux·sec) were measured in the same manner as described above after fatigue of making of 5,000 copies.

The results are shown in TABLE 51.

                  TABLE 51                                                         ______________________________________                                                    Vm (V) after                                                                            E.sub. 1/2 (lux · sec)                                       fatigue  after fatigue                                              ______________________________________                                         Example I-1  480        1.01                                                   Example I-20 1150       0.98                                                   Example I-28 840        0.49                                                   ______________________________________                                    

As is apparent from the above results, the charging characteristics of the photoconductor are excellent when the oxidation potential of the charge transporting material for use in the photoconductor is +0.5 V (vs SCE) or more.

In addition, the electrophotographic photoconductors Nos. I-18 to I-32 employing the charge transporting materials of formulas (14), (15), (17), (19), (22), (23), (24), (28), (29), (30) and (31) show excellent charging characteristics and advantageous photosensitivity.

Furthermore, the charging stability of the electrophotographic photoconductor No. I-21 according to the present invention employing the charge transporting material of formula (17) is excellent even after the repeated operations.

COMPARATIVE EXAMPLE I-4

An unsymmetrical disazo pigment of formula (1) in which R¹ and R² are hydrogen was prepared using the couplers No. 17 and No. 24 shown in TABLE 1. A trisazo pigment of formula (2) in which R³ is hydrogen was prepared using the coupler No. 70 shown in TABLE 2.

Five parts by weight of the disazo pigment and 5 parts by weight of the trisazo pigment were dispersed in a ball mill together with 70 parts by weight of cyclohexanone for 5 days, and further diluted with 420 parts by weight of cyclohexanone. Thus, a coating liquid for a charge generation layer was obtained.

The thus obtained charge generation layer coating liquid was coated on an aluminum plate (Trademark "A1080", made by Sumitomo Light Metal Industries, Ltd.) with a thickness of 0.2 mm by blade coating, dried at 100° C. for 10 minutes, so that a charge generation layer with a thickness of 0.3 μm was formed on the electroconductive support.

A mixture of 100 parts by weight of Z type polycarbonate with a molecular weight of 60,000, 80 parts by weight of 4-diethylaminobenzaldehyde-1-benzyl-1-phenylhydrazone serving as the charge transporting material, and 0.1 parts by weight of a commercially available silicone oil (Trademark "KF-50", made by Shin-Etsu Chemical Co., Ltd.) was dissolved in 300 parts by weight of dichloromethane. Thus, a coating liquid for a charge transport layer was obtained.

The above obtained charge transport layer coating liquid was coated on the charge generation layer by blade coating, and dried at 150° C. for 20 minutes, so that a charge transport layer with a thickness of 20 μm was formed on the charge generation layer.

Thus, a comparative electrophotographic photoconductor No. I-4 of laminated type was obtained.

The spectral sensitivities of the comparative photoconductor No. I-4 of laminated type and the electrophotographic photoconductor No. I-17 according to the present invention were measured by the following method: The comparative photoconductor No. I-4 and the photoconductor No. I-17 according to the present invention were respectively charged to -600 V and +600 V. The monochromatic light was taken out of the lights ranging from 900 to 400 nm by 20 nm using a commercially available monochromator, made by Nikon Corporation, and applied to each photoconductor. The exposure to reduce the surface potential just before the exposure to 1/2 the surface potential was measured as changing the wavelength of the monochromatic light used for the exposure, and the spectral sensitivities (V·cm² /μJ) were calculated from the exposures. The results are shown in FIG. 6.

As is apparent from the graph in FIG. 6, the spectral sensitivity of the electrophotographic photoconductor No. I-17 according to the present invention is remarkably stable in a broad wave range from the light of a high wavelength extending to the light of a low wavelength, as compared with the comparative laminated electrophotographic photoconductor No. I-4.

EXAMPLE II-1

An unsymmetrical disazo pigment of formula (1) in which R¹ and R² are hydrogen was prepared using the couplers No. 17 and No. 24 shown in TABLE 1. A trisazo pigment of formula (2) in which R³ is hydrogen was prepared using the coupler No. 70 shown in TABLE 2.

Five parts by weight of the disazo pigment and 5 parts by weight of the trisazo pigment were dispersed in a ball mill together with 70 parts by weight of tetrahydrofuran for 5 days, and simultaneously pulverized.

The above prepared mixture was added to a solution consisting of 100 parts by weight of Z type polycarbonate with a molecular weight of 60,000, 300 parts by weight of tetrahydrofuran, 50 parts by weight a stilbene compound serving as the organic positive hole transporting material of the following formula (a); ##STR2017## 20 parts by weight of an organic acceptor compound of the following formula (b); ##STR2018## and 0.1 parts by weight of a commercially available silicone oil (Trademark "KF-50", made by Shin-Etsu Chemical Co., Ltd.). Thus, a coating liquid for a photoconductive layer was obtained.

The thus obtained photoconductive layer coating liquid was coated on an aluminum plate (Trademark "A1080", made by Sumitomo Light Metal Industries, Ltd.) with a thickness of 0.2 mm by blade coating, dried at 150° C. for 20 minutes, so that a photoconductive layer with a thickness of 20 μm was formed on the electroconductive support.

Thus, an electrophotographic photoconductor No. II-1 according to the present invention was obtained.

EXAMPLE II-2

The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the unsymmetrical disazo pigment for use in the photoconductive layer coating liquid in Example II-1 was replaced by a disazo pigment of formula (1) (R¹ =R² =hydrogen) which was prepared using the coupler No. 30 shown in TABLE 1.

Thus, an electrophotographic photoconductor No. II-2 according to the present invention was obtained.

EXAMPLE II-3

The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the trisazo pigment for use in the photoconductive layer coating liquid in Example II-1 was replaced by a trisazo pigment of formula (2) (R³ =hydrogen) which was prepared using the coupler No. 214 shown in TABLE 13.

Thus, an electrophotographic photoconductor No. II-3 according to the present invention was obtained.

EXAMPLE II-4

The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the unsymmetrical disazo pigment for use in the photoconductive layer coating liquid in Example II-1 was replaced by a symmetrical disazo pigment of formula (1) (R¹ =R² =hydrogen) which was prepared using the coupler No. 17 shown in TABLE 1.

Thus, an electrophotographic photoconductor No. II-4 according to the present invention was obtained.

EXAMPLE II-5

The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the trisazo pigment for use in the photoconductive layer coating liquid in Example II-1 was replaced by a trisazo pigment of formula (2) (R³ =hydrogen) which was prepared using the coupler No. 3 shown in TABLE 1.

Thus, an electrophotographic photoconductor No. II-5 according to the present invention was obtained.

EXAMPLE II-6

The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example II-1 were separately changed to 0.04 parts by weight.

Thus, an electrophotographic photoconductor No. II-6 according to the present invention was obtained.

EXAMPLE II-7

The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example II-1 were separately changed to 0.05 parts by weight.

Thus, an electrophotographic photoconductor No. II-7 according to the present invention was obtained.

EXAMPLE II-8

The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example II-1 were separately changed to 50 parts by weight.

Thus, an electrophotographic photoconductor No. II-8 according to the present invention was obtained.

EXAMPLE II-9

The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example II-1 were separately changed to 75 parts by weight.

Thus, an electrophotographic photoconductor No. II-9 according to the present invention was obtained.

EXAMPLE II-10

The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example II-1 was changed to 5 parts by weight.

Thus, an electrophotographic photoconductor No. II-10 according to the present invention was obtained.

EXAMPLE II-11

The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example II-1 was changed to 10 parts by weight.

Thus, an electrophotographic photoconductor No. II-11 according to the present invention was obtained.

EXAMPLE II-12

The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example II-1 was changed to 150 parts by weight.

Thus, an electrophotographic photoconductor No. II-12 according to the present invention was obtained.

EXAMPLE II-13

The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example II-1 was changed to 200 parts by weight.

Thus, an electrophotographic photoconductor No. II-13 according to the present invention was obtained.

EXAMPLES II-14 TO II-27

The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the organic acceptor compound for use in the photoconductive layer coating liquid in Example II-1 was replaced by the respective organic acceptor compounds as shown in TABLE 52.

Thus, electrophotographic photoconductors Nos. II-14 to II-27 according to the present invention were obtained.

The dynamic electrostatic properties of each of the electrophotographic photoconductors No. II-1 to No. II-27 according to the present invention were measured by using a commercially available test apparatus (Trademark "EPA-8100", made by Kawaguchi Electro Works Co., Ltd.) under the circumstances of 25° C. and 50% RH.

More specifically, each photoconductor was charged positively in the dark under application of +6 kV for 10 seconds. Then, each photoconductor was allowed to stand in the dark for 20 seconds without applying any charge thereto. After that, the photoconductor was illuminated by a 780 nm-monochromatic light in such a manner that the illuminated surface of the photoconductor was 10 μW/cm².

The surface potential V_(s) (V) which was obtained ten seconds after the initiation of charging; the surface potential V_(o) (V) which was obtained after the dark decay; and the exposure E_(1/2) (μJ/cm²) required to reduce the surface potential V_(o) to 1/2 the surface potential V_(o) were measured. In addition, to evaluate the charging characteristics after the repeated electrophotographic processes, the surface potentials V_(s) and V_(o), and the exposure E_(1/2) were measured after making of 5,000 copies.

The results are shown in TABLE 52.

                                      TABLE 52                                     __________________________________________________________________________                            Acceptor                   After making 5000            Disazo    Trisazo                                                                             Azo Pigments/                                                                          Compound/                                                                             Acceptor                                                                               Initial Stage                                                                              copies                       Coupler   Coupler                                                                             Binder Resin                                                                           Binder Compound                                                                               V.sub.s                                                                           V.sub.0                                                                            E.sub.1/2                                                                           V.sub.s                                                                            V.sub.0                                                                           E.sub.1/2             No.       No.  Ratio   Resin Ratio                                                                           No.     (V)                                                                               (V) (μJ/cm.sup.2)                                                                    (V) (V)                                                                               (μJ/cm.sup.2)      __________________________________________________________________________     Ex. II-1                                                                            17, 24                                                                              70   1/10    2/10   (b)     1530                                                                              1150                                                                               0.52 1510                                                                               1110                                                                              0.54                  Ex. II-2                                                                            30   70   1/10    2/10   (b)     1510                                                                              1120                                                                               0.60 1500                                                                               1080                                                                              0.60                  Ex. II-3                                                                            17, 24                                                                              214  1/10    2/10   (b)     1480                                                                              1090                                                                               0.55 1450                                                                               1080                                                                              0.56                  Ex. II-4                                                                            17   70   1/10    2/10   (b)     1500                                                                              1140                                                                               0.68 1480                                                                               1110                                                                              0.69                  Ex. II-5                                                                            17, 24                                                                               3   1/10    2/10   (b)     1610                                                                              1220                                                                               0.63 1590                                                                               1190                                                                              0.63                  Ex. II-6                                                                            17, 24                                                                              70   0.008/10                                                                               2/10   (b)     1780                                                                              1330                                                                               0.85 1760                                                                               1280                                                                              0.87                  Ex. II-7                                                                            17, 24                                                                              70   0.01/10 2/10   (b)     1750                                                                              1270                                                                               0.71 1710                                                                               1230                                                                              0.71                  Ex. II-8                                                                            17, 24                                                                              70   10/10   2/10   (b)     1300                                                                              1020                                                                               0.48 1280                                                                                990                                                                              0.48                  Ex. II-9                                                                            17, 24                                                                              70   15/10   2/10   (b)     1140                                                                              830 0.45 1130                                                                                810                                                                              0.45                  Ex. II-10                                                                           17, 24                                                                              70   1/10    0.5/10 (b)     1520                                                                              1130                                                                               0.43 1300                                                                                980                                                                              0.52                  Ex. II-11                                                                           17, 24                                                                              70   1/10    1/10   (b)     1490                                                                              1080                                                                               0 .47                                                                               1470                                                                               1020                                                                              0.51                  Ex. II-12                                                                           17, 24                                                                              70   1/10    15/10  (b)     1380                                                                              1050                                                                               0.80 1380                                                                               1040                                                                              0.80                  Ex. II-13                                                                           17, 24                                                                              70   1/10    20/10  (b)     1310                                                                               990                                                                               1.25 1300                                                                                990                                                                              1.23                  Ex. II-14                                                                           17, 24                                                                              70   1/10    2/10   (1)-18  1550                                                                              1160                                                                               0.65 1510                                                                               1120                                                                              0.60                                                (TABLE 17)                                       Ex. II-15                                                                           17, 24                                                                              70   1/10    2/10   (2)-74  1490                                                                              1100                                                                               0.56 1440                                                                               1080                                                                              0.55                                                (TABLE 18)                                       Ex. II-16                                                                           17, 24                                                                              70   1/10    2/10   (3)-152 1350                                                                              1070                                                                               0.53 1330                                                                               1070                                                                              0.53                                                (TABLE 19)                                       Ex. II-17                                                                           17, 24                                                                              70   1/10    2/10   (4)-1   1510                                                                              1170                                                                               0.66 1470                                                                               1090                                                                              0.68                                                (TABLE 20)                                       Ex. II-18                                                                           17, 24                                                                              70   1/10    2110   (5)-22  1330                                                                              1010                                                                               0.57 1310                                                                                990                                                                              0.62                                                (TABLE 21)                                       Ex. II-19                                                                           17, 24                                                                              70   1/10    2/10   (6)-5   1450                                                                              1220                                                                               0.71 1410                                                                               1180                                                                              0.73                                                (TABLE 22)                                       Ex. II-20                                                                           17, 24                                                                              70   1/10    2/10   (7)-10  1530                                                                              1190                                                                               0.63 1520                                                                               1170                                                                              0.69                                                (TABLE 23)                                       Ex. II-21                                                                           17, 24                                                                              70   1/10    2/10   (8)-83  1490                                                                              1280                                                                               0.66 1420                                                                               1250                                                                              0.59                                                (TABLE 24)                                       Ex. II-22                                                                           17, 24                                                                              70   1/10    2/10   (9)-102 1590                                                                              1230                                                                               0.51 1550                                                                               1200                                                                              0.62                                                (TABLE 25)                                       Ex. II-23                                                                           17, 24                                                                              70   1/10    2/10   (10)-6  1680                                                                              1390                                                                               0.70 1650                                                                               1370                                                                              0.76                                                (TABLE 26)                                       Ex. II-24                                                                           17, 24                                                                              70   1/10    2/10   (11)-2  1620                                                                              1400                                                                               0.62 1580                                                                               1330                                                                              0.66                                                (TABLE 27)                                       Ex. II-25                                                                           17, 24                                                                              70   1/10    2/10   (12)-5  1610                                                                              1330                                                                               0.58 1580                                                                               1290                                                                              0.64                                                (TABLE 28)                                       Ex. II-26                                                                           17, 24                                                                              70   1/10    2/10   (13)-13 1630                                                                              1370                                                                               0.61 1590                                                                               1360                                                                              0.73                                                (TABLE 29)                                       Ex. II-27                                                                           17, 24                                                                              70   1/10    2/10   (14)-27 1510                                                                              1200                                                                               0.54 1480                                                                               1150                                                                              0.63                                                (TABLE 30)                                       __________________________________________________________________________

As previously explained, the electrophotographic photoconductors according to the present invention exhibit high photosensitivity in a broad wave range from the visible region extending to the near infrared region, and excellent charging stability when the single-layered photoconductive layer comprises a simultaneously pulverized mixture comprising the disazo pigment of formula (1) and the trisazo pigment of formula (2), the organic positive hole transporting material, the organic acceptor compound, and the binder resin.

EXAMPLE III-1

An unsymmetrical disazo pigment of formula (1) in which R¹ and R² are hydrogen was prepared using the couplers No. 17 and No. 24 shown in TABLE 1. A trisazo pigment of formula (2) in which R³ is hydrogen was prepared using the coupler No. 70 shown in TABLE 2.

Five parts by weight of the disazo pigment and 5 parts by weight of the trisazo pigment were dispersed in a ball mill together with 70 parts by weight of tetrahydrofuran for 5 days, and simultaneously pulverized.

The above prepared mixture was added to a solution consisting of 100 parts by weight of Z type polycarbonate with a molecular weight of 60,000, 300 parts by weight of tetrahydrofuran, 50 parts by weight a stilbene compound serving as an organic positive hole transporting material of the following formula (a); ##STR2019## 20 parts by weight of an organic acceptor compound No. B-2 in TABLE 32, and 0.1 parts by weight of a commercially available silicone oil (Trademark "KF-50", made by Shin-Etsu Chemical Co., Ltd.). Thus, a coating liquid for a photoconductive layer was obtained.

The thus obtained photoconductive layer coating liquid was coated on an aluminum plate (Trademark "A1080", made by Sumitomo Light Metal Industries, Ltd.) with a thickness of 0.2 mm by blade coating, dried at 150° C. for 20 minutes, so that a photoconductive layer with a thickness of 20 μm was formed on the electroconductive support.

Thus, an electrophotographic photoconductor No. III-1 according to the present invention was obtained.

EXAMPLE III-2

The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the unsymmetrical disazo pigment for use in the photoconductive layer coating liquid in Example III-1 was replaced by a disazo pigment of formula (1) (R¹ =R² =hydrogen) which was prepared using the coupler No. 30 shown in TABLE 1.

Thus, an electrophotographic photoconductor No. III-2 according to the present invention was obtained.

EXAMPLE III-3

The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the trisazo pigment for use in the photoconductive layer coating liquid in Example III-1 was replaced by a trisazo pigment of formula (2) (R³ =hydrogen) which was prepared using the coupler No. 214 shown in TABLE 13.

Thus, an electrophotographic photoconductor No. III-3 according to the present invention was obtained.

EXAMPLE III-4

The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the unsymmetrical disazo pigment for use in the photoconductive layer coating liquid in Example III-1 was replaced by a disazo pigment of formula (1) (R¹ =R² =hydrogen) which was prepared using the coupler No. 17 shown in TABLE 1.

Thus, an electrophotographic photoconductor No. III-4 according to the present invention was obtained.

EXAMPLE III-5

The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the trisazo pigment for use in the photoconductive layer coating liquid in Example III-1 was replaced by a trisazo pigment of formula (2) (R³ =hydrogen) which was prepared using the coupler No. 3 shown in TABLE 1.

Thus, an electrophotographic photoconductor No. III-5 according to the present invention was obtained.

EXAMPLE III-6

The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example III-1 were separately changed to 0.04 parts by weight.

Thus, an electrophotographic photoconductor No. III-6 according to the present invention was obtained.

EXAMPLE III-7

The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example III-1 were separately changed to 0.05 parts by weight.

Thus, an electrophotographic photoconductor No. III-7 according to the present invention was obtained.

EXAMPLE III-8

The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example III-1 were separately changed to 50 parts by weight.

Thus, an electrophotographic photoconductor No. III-8 according to the present invention was obtained.

EXAMPLE III-9

The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example III-1 were separately changed to 75 parts by weight.

Thus, an electrophotographic photoconductor No. III-9 according to the present invention was obtained.

EXAMPLE III-10

The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example III-1 was changed to 5 parts by weight.

Thus, an electrophotographic photoconductor No. III-10 according to the present invention was obtained.

EXAMPLE III-11

The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example III-1 was changed to 10 parts by weight.

Thus, an electrophotographic photoconductor No. III-11 according to the present invention was obtained.

EXAMPLE III-12

The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example III-1 was changed to 150 parts by weight.

Thus, an electrophotographic photoconductor No. III-12 according to the present invention was obtained.

EXAMPLE III-13

The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example III-1 was changed to 200 parts by weight. Thus, an electrophotographic photoconductor No. III-13 according to the present invention was obtained.

EXAMPLES III-14 TO III-16

The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the organic acceptor compound for use in the photoconductive layer coating liquid in Example III-1 was replaced by the respective organic acceptor compounds as shown in TABLE 53.

Thus, electrophotographic photoconductors Nos. III-14 to III-16 according to the present invention were obtained.

                  TABLE 53                                                         ______________________________________                                                        Organic Acceptor                                                               Compound                                                        ______________________________________                                         Example III-14   Compound No. A-3                                              Example III-15   Compound No. B-29                                             Example III-16   Compound No. CIII-11                                          ______________________________________                                    

The dynamic electrostatic properties of each of the electrophotographic photoconductors No. III-1 to No. III-16 according to the present invention were measured by using a commercially available test apparatus (Trademark "EPA-8100", made by Kawaguchi Electro Works Co., Ltd.) under the circumstances of 25° C. and 50% RH.

More specifically, each photoconductor was charged positively in the dark under application of +6 kV for 10 seconds. Then, each photoconductor was allowed to stand in the dark for 20 seconds without applying any charge thereto. After that, the photoconductor was illuminated by a 780 nm-monochromatic light in such a manner that the illuminance on the illuminated surface of the photoconductor was 10 μW/cm².

The surface potential V_(s) (V) which was obtained ten seconds after the initiation of charging; the surface potential V_(o) (V) which was obtained after the dark decay; and the exposure E_(1/2) (μJ/cm²) required to reduce the surface potential V_(o) to 1/2 the surface potential V_(o) were measured. In addition, to evaluate the charging characteristics after the repeated electrophotographic processes, the surface potentials V_(s) and V_(o), and the exposure E_(1/2) were measured after making of 5,000 copies.

The results are shown in TABLE 54.

                                      TABLE 54                                     __________________________________________________________________________                             Acceptor                  After making 5000            Disazo     Trisazo                                                                             Azo Pigments/                                                                          Compound/                                                                             Acceptor                                                                              Initial Stage                                                                              copies                       Coupler    Coupler                                                                             Binder Resin                                                                           Binder Compound                                                                              V.sub.s                                                                           V.sub.0                                                                            E.sub.1/2                                                                           V.sub.s                                                                            V.sub.0                                                                           E.sub.1/2             No.        No.  Ratio   Resin Ratio                                                                           No.    (V)                                                                               (V) (μJ/cm.sup.2)                                                                    (V) (V)                                                                               (μJ/cm.sup.2)      __________________________________________________________________________     Ex. III-1                                                                            17, 24                                                                              70   1/10    2/10   B-2    1690                                                                              1300                                                                               0.59 1660                                                                               1260                                                                              0.60                  Ex. III-2                                                                            30   70   1/10    2/10   B-2    1620                                                                              1280                                                                               0.62 1600                                                                               1240                                                                              0.64                  Ex. III-3                                                                            17, 24                                                                              214  1/10    2/10   B-2    1520                                                                              1110                                                                               0.57 1490                                                                               1120                                                                              0.58                  Ex. III-4                                                                            17   70   1/10    2/10   B-2    1580                                                                              1190                                                                               0.68 1520                                                                               1170                                                                              0.71                  Ex. III-5                                                                            17, 24                                                                               3   1/10    2/10   B-2    1730                                                                              1290                                                                               0.65 1670                                                                               1210                                                                              0.68                  Ex. III-6                                                                            17, 24                                                                              70   0.008/10                                                                               2/10   B-2    1810                                                                              1360                                                                               0.88 1790                                                                               1330                                                                              0.90                  Ex. III-7                                                                            17, 24                                                                              70   0.01/10 2/10   B-2    1770                                                                              1340                                                                               0.75 1720                                                                               1290                                                                              0.75                  Ex. III-8                                                                            17, 24                                                                              70   10/10   2/10   B-2    1320                                                                              1050                                                                               0.49 1290                                                                               1010                                                                              0.51                  Ex. III-9                                                                            17, 24                                                                              70   15/10   2/10   B-2    1180                                                                               850                                                                               0.44 1150                                                                                820                                                                              0.46                  Ex. III-10                                                                           17, 24                                                                              70   1/10    0.5/10 B-2    1580                                                                              1190                                                                               0.43 1340                                                                               1160                                                                              0.47                  Ex. III-11                                                                           17, 24                                                                              70   1/10    1/10   B-2    1540                                                                              1210                                                                               0.50 1520                                                                               1180                                                                              0.54                  Ex. III-12                                                                           17, 24                                                                              70   1/10    15/10  B-2    1420                                                                              1090                                                                               0.82 1410                                                                               1040                                                                              0.82                  Ex. III-13                                                                           17, 24                                                                              70   1/10    20/10  B-2    1380                                                                              1030                                                                               1.31 1320                                                                                990                                                                              1.30                  Ex. III-14                                                                           17, 24                                                                              70   1/10    2/10   A-3    1520                                                                              1180                                                                               0.60 1480                                                                               1090                                                                              0.64                  Ex. III-15                                                                           17, 24                                                                              70   1/10    2/10    B-23  1680                                                                              1340                                                                               0.65 1620                                                                               1290                                                                              0.71                  Ex. III-16                                                                           17, 24                                                                              70   1/10    2/10   CIII-11                                                                               1490                                                                              1160                                                                               0.54 1430                                                                               1110                                                                              0.55                  __________________________________________________________________________

As previously explained, the electrophotographic photoconductors according to the present invention exhibit high photosensitivity in a broad wave range from the visible region extending to the near infrared region, and excellent charging stability when the single-layered photoconductive layer comprises a simultaneously pulverized mixture comprising the disazo pigment of formula (1) and the trisazo pigment of formula (2), the organic positive hole transporting material, the specified organic acceptor compound, and the binder resin.

EXAMPLE IV-1

An unsymmetrical disazo pigment of formula (1) in which R¹ and R² are hydrogen was prepared using the couplers No. 17 and No. 24 shown in TABLE 1. A trisazo pigment of formula (2) in which R¹ is hydrogen was prepared using the coupler No. 70 shown in TABLE 2.

Five parts by weight of the disazo pigment and 5 parts by weight of the trisazo pigment were dispersed in a ball mill together with 70 parts by weight of tetrahydrofuran for 5 days, and simultaneously pulverized.

The above prepared mixture was added to a solution consisting of 100 parts by weight of Z type polycarbonate with a molecular weight of 60,000, 300 parts by weight of tetrahydrofuran, 50 parts by weight a stilbene compound serving as the organic positive hole transporting material of the following formula (a); ##STR2020## 20 parts by weight of an organic acceptor compound the following formula (c) with a reduction potential of -0.47 v (vs SCE); ##STR2021## and 0.1 parts by weight of a commercially available silicone oil (Trademark "KF-50", made by Shin-Etsu Chemical Co., Ltd.). Thus, a coating liquid for a photoconductive layer was obtained.

The thus obtained photoconductive layer coating liquid was coated on an aluminum plate (Trademark "A1080", made by Sumitomo Light Metal Industries, Ltd.) with a thickness of 0.2 mm by blade coating, dried at 150° C. for 20 minutes, so that a photoconductive layer with a thickness of 20 μm was formed on the electroconductive support.

Thus, an electrophotographic photoconductor No. IV-1 according to the present invention was obtained.

EXAMPLE IV-2

The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the unsymmetrical disazo pigment for use in the photoconductive layer coating liquid in Example IV-1 was replaced by a disazo pigment of formula (1) (R¹ =R² =hydrogen) which was prepared using the coupler No. 30 shown in TABLE 1.

Thus, an electrophotographic photoconductor No. IV-2 according to the present invention was obtained.

EXAMPLE IV-3

The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the trisazo pigment for use in the photoconductive layer coating liquid in Example IV-1 was replaced by a trisazo pigment of formula (2) (R³ =hydrogen) which was prepared using the coupler No. 214 shown in TABLE 13.

Thus, an electrophotographic photoconductor No. IV-3 according to the present invention was obtained.

EXAMPLE IV-4

The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the unsymmetrical disazo pigment for use in the photoconductive layer coating liquid in Example IV-1 was replaced by a symmetrical disazo pigment of formula (1) (R¹ =R² =hydrogen) which was prepared using the coupler No. 17 shown in TABLE 1.

Thus, an electrophotographic photoconductor No. IV-4 according to the present invention was obtained.

EXAMPLE IV-5

The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the trisazo pigment for use in the photoconductive layer coating liquid in Example IV-1 was replaced by a trisazo pigment of formula (2) (R³ =hydrogen) which was prepared using the coupler No. 3 shown in TABLE 1.

Thus, an electrophotographic photoconductor No. IV-5 according to the present invention was obtained.

EXAMPLE IV-6

The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example IV-1 were separately changed to 0.04 parts by weight.

Thus, an electrophotographic photoconductor No. IV-6 according to the present invention was obtained.

EXAMPLE IV-7

The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example IV-1 were separately changed to 0.05 parts by weight.

Thus, an electrophotographic photoconductor No. IV-7 according to the present invention was obtained.

EXAMPLE IV-8

The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example IV-1 were separately changed to 50 parts by weight.

Thus, an electrophotographic photoconductor No. IV-8 according to the present invention was obtained.

EXAMPLE IV-9

The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example IV-1 were separately changed to 75 parts by weight.

Thus, an electrophotographic photoconductor No. IV-9 according to the present invention was obtained.

EXAMPLE IV-10

The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example IV-1 was changed to 5 parts by weight.

Thus, an electrophotographic photoconductor No. IV-10 according to the present invention was obtained.

EXAMPLE IV-11

The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example IV-1 was changed to 10 parts by weight.

Thus, an electrophotographic photoconductor No. IV-11 according to the present invention was obtained.

EXAMPLE IV-12

The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example IV-1 was changed to 150 parts by weight.

Thus, an electrophotographic photoconductor No. IV-12 according to the present invention was obtained.

EXAMPLE IV-13

The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example IV-1 was changed to 200 parts by weight.

Thus, an electrophotographic photoconductor No. IV-13 according to the present invention was obtained.

EXAMPLES IV-14 TO IV-20

The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the organic acceptor compound for use in the photoconductive layer coating liquid in Example IV-1 was replaced by the respective organic acceptor compounds as shown in TABLE 55.

Thus, electrophotographic photoconductors Nos. IV-14 to IV-20 according to the present invention were obtained.

                                      TABLE 55                                     __________________________________________________________________________                                  Reduction                                                                      Potential                                         Organic Acceptor Compound    [(V (vs SCE)]                                     __________________________________________________________________________     Ex. IV-14                                                                             ##STR2022##           -0.41                                             Ex. IV-15                                                                             ##STR2023##           -0.59                                             Ex. IV-16                                                                             ##STR2024##           -0.87                                             Ex. IV-17                                                                             ##STR2025##           -0.92                                             Ex. IV-18                                                                             ##STR2026##           -1.06                                             Ex. IV-19                                                                             ##STR2027##           -0.15                                             Ex. IV-20                                                                             ##STR2028##           -1.42                                             __________________________________________________________________________

COMPARATIVE EXAMPLE IV-1

An unsymmetrical disazo pigment of formula (1) in which R¹ and R² are hydrogen was prepared using the couplers No. 17 and No. 24 shown in TABLE 1. A trisazo pigment of formula (2) in which R³ is hydrogen was prepared using the coupler No. 70 shown in TABLE 2.

Five parts by weight of the disazo pigment and 5 parts by weight of the trisazo pigment were separately dispersed in a ball mill with 35 parts by weight of tetrahydrofuran for 5 days. Then, the dispersion of the disazo pigment and the dispersion of the trisazo pigment were mixed.

The above prepared mixture was added to a solution consisting of 100 parts by weight of Z type polycarbonate with a molecular weight of 60,000, 300 parts by weight of tetrahydrofuran, 80 parts by weight of the same organic positive hole transporting material as used in Example IV-1, 20 parts by weight of the same organic acceptor compound as used in Example IV-1, and 0.1 parts by weight of a commercially available silicone oil (Trademark "KF-50", made by Shin-Etsu Chemical Co., Ltd.). Thus, a coating liquid for a photoconductive layer was obtained.

The thus obtained photoconductive layer coating liquid was coated on an aluminum plate (Trademark "A1080", made by Sumitomo Light Metal Industries, Ltd.) with a thickness of 0.2 mm by blade coating, dried at 150° C. for 20 minutes, so that a photoconductive layer with a thickness of 20 μm was formed on the electroconductive support.

Thus, a comparative electrophotographic photoconductor No. IV-1 was obtained.

COMPARATIVE EXAMPLE IV-2

The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the trisazo pigment of formula (2) prepared by use of the coupler No. 70 was not employed in the preparation of the photoconductive layer coating liquid.

Thus, a comparative electrophotographic photoconductor No. IV-2 was obtained.

COMPARATIVE EXAMPLE IV-3

The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the unsymmetrical disazo pigment of formula (1) prepared by use of the couplers Nos. 17 and 24 was not employed in the preparation of the photoconductive layer coating liquid.

Thus, a comparative electrophotographic photoconductor No. IV-3 was obtained.

The dynamic electrostatic properties and the charging characteristics after the repeated electrophotographic processes of each of the electrophotographic photoconductors No. IV-1 to No. IV-20 according to the present invention and the comparative electrophotographic photoconductors No. IV-1 to No. IV-3 were measured in the same manner as in Example II-1.

The results are shown in TABLE 56.

                                      TABLE 56                                     __________________________________________________________________________                             Acceptor          After making 5000                    Disazo     Trisazo                                                                             Azo Pigments/                                                                          Compound/                                                                             Initial Stage                                                                             copies                               Coupler    Coupler                                                                             Binder Resin                                                                           Binder V.sub.s                                                                           V.sub.0                                                                           E.sub. 1/2                                                                          V.sub.s                                                                           V.sub.0                                                                           E.sub. 1/2                     No.        No.  Ratio   Resin Ratio                                                                           (V)                                                                               (V)                                                                               (μJ/cm.sup.2)                                                                    (V)                                                                               (V)                                                                               (μJ/cm.sup.2)               __________________________________________________________________________     Ex. IV-1                                                                             17, 24                                                                              70   1/10    2110   1510                                                                              1140                                                                              0.49 1490                                                                              1100                                                                              0.51                           Ex. IV-2                                                                             30   70   1/10    2/10   1470                                                                              1100                                                                              0.56 1450                                                                              1070                                                                              0.56                           Ex. IV-3                                                                             17, 24                                                                              214  1/10    2/10   1450                                                                              1080                                                                              0.53 1410                                                                              1060                                                                              0.54                           Ex. IV-4                                                                             17   70   1/10    2/10   1480                                                                              1120                                                                              0.65 1440                                                                              1090                                                                              0.67                           Ex. IV-5                                                                             17, 24                                                                               3   1/10    2/10   1580                                                                              1240                                                                              0.60 1550                                                                              1200                                                                              0.59                           Ex. IV-6                                                                             17, 24                                                                              70   0.008/10                                                                               2/10   1690                                                                              1300                                                                              0.80 1660                                                                              1240                                                                              0.82                           Ex. IV-7                                                                             17, 24                                                                              70   0.01/10 2/10   1660                                                                              1230                                                                              0.69 1650                                                                              1190                                                                              0.71                           Ex. IV-8                                                                             17, 24                                                                              70   10/10   2/10   1290                                                                              1000                                                                              0.45 1250                                                                               970                                                                              0.45                           Ex. IV-9                                                                             17, 24                                                                              70   15/10   2/10   1110                                                                               820                                                                              0.42 1090                                                                               800                                                                              0.42                           Ex. IV-10                                                                            17, 24                                                                              70   1/10    0.5/10 1490                                                                              1090                                                                              0.43 1020                                                                               830                                                                              0.40                           Ex. IV-11                                                                            17, 24                                                                              70   1/10    1/10   1460                                                                              1050                                                                              0.44 1450                                                                              1040                                                                              0.46                           Ex. IV-12                                                                            17, 24                                                                              70   1/10    15/10  1360                                                                              1020                                                                              0.76 1340                                                                              1000                                                                              0.75                           Ex. IV-13                                                                            17, 24                                                                              70   1/10    20/10  1280                                                                               970                                                                              1.22 1210                                                                               920                                                                              1.24                           Ex. IV-14                                                                            17, 24                                                                              70   1/10    2/10   1530                                                                              1250                                                                              0.55 1500                                                                              1210                                                                              0.56                           Ex. IV-15                                                                            17, 24                                                                              70   1/10    2/10   1460                                                                              1270                                                                              0.50 1460                                                                              1260                                                                              0.51                           Ex. IV-16                                                                            17, 24                                                                              70   1/10    2/10   1350                                                                              1100                                                                              0.66 1320                                                                              1070                                                                              0.68                           Ex. IV-17                                                                            17, 24                                                                              70   1/10    2/10   1620                                                                              1490                                                                              0.71 1620                                                                              1480                                                                              0.73                           Ex. IV-18                                                                            17, 24                                                                              70   1/10    2/10   1390                                                                              1100                                                                              0.64 1360                                                                              1070                                                                              0.65                           Comp. 17, 24                                                                              70   1/10    2/10   1400                                                                              1090                                                                              3.55 1350                                                                              1050                                                                              3.72                           Ex. IV-1                                                                       Comp. 17, 24                                                                              None 1/10    2/10   1560                                                                              1330                                                                              No   1550                                                                              1320                                                                              No                             Ex. IV-2                             sensi-     sensi-                                                              tivity     tivity                         Comp. None 70   1/10    2/10   1530                                                                              1370                                                                              2.29 1500                                                                              1330                                                                              2.60                           Ex. IV-3                                                                       Ex. IV-19                                                                            17, 24                                                                              70   1/10    2/10   1490                                                                              1170                                                                              1.85 1460                                                                              1160                                                                              1.84                           Ex. IV-20                                                                            17, 24                                                                              70   1/10    2/10   1620                                                                              1390                                                                              3.14  820                                                                               510                                                                              3.95                           __________________________________________________________________________

As previously explained, the electrophotographic photoconductors according to the present invention exhibit high photosensitivity in a broad wave range from the visible region extending to the near infrared region, and excellent charging stability when the single-layered photoconductive layer comprises a simultaneously pulverized mixture comprising the disazo pigment of formula (1) and the trisazo pigment of formula (2), the organic positive hole transporting material, the organic acceptor compound having a reduction potential in a range of -0.2 to -1.2 V (vs SCE), and the binder resin.

EXAMPLE V-1

Five parts by weight of a disazo pigment of formula (d) and 5 parts by weight of a trisazo pigment of formula (e) were dispersed in a ball mill together with 70 parts by weight of methyl ethyl ketone for 5 days, and simultaneously pulverized. ##STR2029##

The above prepared mixture was added to a solution consisting of 100 parts by weight of Z type polycarbonate with a molecular weight of 60,000, 300 parts by weight of tetrahydrofuran, 80 parts by weight of 4-diethylaminobenzaldehyde-1-benzyl-1-phenylhydrazone serving as the charge transporting material, 5 parts by weight of a commercially available hindered amine compound (Trademark "Sanol LS-770", made by Sankyo Company, Limited) serving as the antioxidant, and 0.1 parts by weight of a commercially available silicone oil (Trademark "KF-50", made by Shin-Etsu Chemical Co., Ltd.). Thus, a coating liquid for a photoconductive layer was obtained.

The thus obtained photoconductive layer coating liquid was coated on an aluminum plate (Trademark "A1080", made by Sumitomo Light Metal Industries, Ltd.) with a thickness of 0.2 mm by blade coating, dried at 150° C. for 20 minutes, so that a photoconductive layer with a thickness of 20 μm was formed on the electroconductive support.

Thus, an electrophotographic photoconductor No. V-1 according to the present invention was obtained.

EXAMPLE V-2

The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the disazo pigment of formula (d) for use in the photoconductive layer coating liquid in Example V-1 was replaced by a disazo pigment of the following formula (f): ##STR2030##

Thus, an electrophotographic photoconductor No. V-2 according to the present invention was obtained.

EXAMPLE V-3

The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the trisazo pigment of formula (e) for use in the photoconductive layer coating liquid in Example V-1 was replaced by a trisazo pigment of the following formula (g): ##STR2031##

Thus, an electrophotographic photoconductor No. V-3 according to the present invention was obtained.

EXAMPLE V-4

The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the disazo pigment of formula (d) for use in the photoconductive layer coating liquid in Example V-1 was replaced by a disazo pigment of the following formula (h): ##STR2032##

Thus, an electrophotographic photoconductor No. V-4 according to the present invention was obtained.

EXAMPLE V-5

The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the trisazo pigment of formula (e) for use in the photoconductive layer coating liquid in Example V-1 was replaced by a trisazo pigment of the following formula (i): ##STR2033##

Thus, an electrophotographic photoconductor No. V-5 according to the present invention was obtained.

EXAMPLE V-6

The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the amount of the disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example V-1 were separately changed to 0.04 parts by weight.

Thus, an electrophotographic photoconductor No. V-6 according to the present invention was obtained.

EXAMPLE V-7

The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the amount of the disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example V-1 were separately changed to 0.05 parts by weight.

Thus, an electrophotographic photoconductor No. V-7 according to the present invention was obtained.

EXAMPLE V-8

The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the amount of the disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example V-1 were separately changed to 50 parts by weight.

Thus, an electrophotographic photoconductor No. V-8 according to the present invention was obtained.

EXAMPLE V-9

The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the amount of the disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example V-1 were separately changed to 75 parts by weight.

Thus, an electrophotographic photoconductor No. V-9 according to the present invention was obtained.

EXAMPLE V-10

The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the amount of the charge transporting material for use in the photoconductive layer coating liquid in Example V-1 was changed to 5 parts by weight.

Thus, an electrophotographic photoconductor No. V-10 according to the present invention was obtained.

EXAMPLE V-11

The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the amount of the charge transporting material for use in the photoconductive layer coating liquid in Example V-1 was changed to 10 parts by weight.

Thus, an electrophotographic photoconductor No. V-11 according to the present invention was obtained.

EXAMPLE V-12

The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the amount of the charge transporting material for use in the photoconductive layer coating liquid in Example V-1 was changed to 150 parts by weight.

Thus, an electrophotographic photoconductor No. V-12 according to the present invention was obtained.

EXAMPLE V-13

The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the amount of the charge transporting material for use in the photoconductive layer coating liquid in Example V-1 was changed to 200 parts by weight.

Thus, an electrophotographic photoconductor No. V-13 according to the present invention was obtained.

EXAMPLE V-14

The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that methyl ethyl ketone used in dispersing the azo pigments in Example V-1 was replaced by 1,4-dioxane.

Thus, an electrophotographic photoconductor No. V-14 according to the present invention was obtained.

EXAMPLE V-15

The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that methyl ethyl ketone used in dispersing the azo pigments in Example V-1 was replaced by isophorone.

Thus, an electrophotographic photoconductor No. V-15 according to the present invention was obtained.

EXAMPLE V-16

The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that methyl ethyl ketone used in dispersing the azo pigments in Example V-1 was replaced by tetrahydrofuran.

Thus, an electrophotographic photoconductor No. V-16 according to the present invention was obtained.

EXAMPLE V-17

The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that methyl ethyl ketone used in dispersing the azo pigments in Example V-1 was replaced by cyclohexanone.

Thus, an electrophotographic photoconductor No. V-17 according to the present invention was obtained.

The dynamic electrostatic properties of each of the electrophotographic photoconductors No. V-1 to No. V-17 according to the present invention were measured in the same manner as in Example I-1.

The results are shown in TABLE 57.

                                      TABLE 57                                     __________________________________________________________________________                                Charge                                                                         Transporting         V.sub.30                                                                             E.sub.1/2                                   Azo Pigments/                                                                          Material/                                                                             Solvent for                                                                             E.sub.1/2                                                                           (mono-                                                                               (mono-                   Disazo      Trisazo                                                                               Binder Resin                                                                           Binder Resin                                                                          dispersing                                                                           V.sub.2                                                                           (white)                                                                             chromatic)                                                                           chromatic)                                                                           V.sub.30           Coupler No. Coupler No.                                                                           Ratio   Ratio  pigments                                                                             V  lux · sec                                                                  V     μJ/cm.sup.2                                                                       V                  __________________________________________________________________________     Ex. V-1                                                                             Formula (d)                                                                           Formula (e)                                                                           1/10    8/10   MEK   720                                                                               1.00 45    0.50  40                 Ex. V-2                                                                             Formula (f)                                                                           Formula (e)                                                                           1/10    8/10   MEK   740                                                                               1.12 40    0.60  40                 Ex. V-3                                                                             Formula (d)                                                                           Formula (g)                                                                           1/10    8/10   MEK   710                                                                               1.18 45    0.62  45                 Ex. V-4                                                                             Formula (h)                                                                           Formula (e)                                                                           1/10    8/10   MEK   690                                                                               1.08 45    0.65  45                 Ex. V-5                                                                             Formula (d)                                                                           Formula (i)                                                                           1/10    8/10   MEK   720                                                                               1.40 60    0.88  55                 Ex. V-6                                                                             Formula (d)                                                                           Formula (e)                                                                           0.008/10                                                                               8/10   MEK   770                                                                               1.15 85    0.62  75                 Ex. V-7                                                                             Formula (d)                                                                           Formula (e)                                                                           0.01/10 8/10   MEK   750                                                                               1.10 75    0.55  60                 Ex. V-8                                                                             Formula (d)                                                                           Formula (e)                                                                           10/10   8/10   MEK   690                                                                               0.97 25    0.47  30                 Ex. V-9                                                                             Formula (d)                                                                           Formula (e)                                                                           15/10   8/10   MEK   580                                                                               0.97 15    0.46  25                 Ex. V-10                                                                            Formula (d)                                                                           Formula (e)                                                                           1/10    0.5/10 MEK   760                                                                               1.12 50    0.62  50                 Ex. V-11                                                                            Formula (d)                                                                           Formula (e)                                                                           1/10    1/10   MEK   735                                                                               1.08 45    0.58  45                 Ex. V-12                                                                            Formula (d)                                                                           Formula (e)                                                                           1/10    15/10  MEK   700                                                                               0.98 40    0.48  35                 Ex. V-13                                                                            Formula (d)                                                                           Formula (e)                                                                           1/10    20/10  MEK   635                                                                               0.99 40    0.48  30                 Ex. V-14                                                                            Formula (d)                                                                           Formula (e)                                                                           1/10    8/10   Dioxane                                                                              650                                                                               0.95 40    0.47  40                 Ex. V-15                                                                            Formula (d)                                                                           Formula (e)                                                                           1/10    8/10   Isophorone                                                                           720                                                                               0.98 40    0.46  40                 Ex. V-16                                                                            Formula (d)                                                                           Formula (e)                                                                           1/10    8/10   THF   715                                                                               0.89 35    0.42  35                 Ex. V-17                                                                            Formula (d)                                                                           Formula (e)                                                                           1/10    8/10   Anone 700                                                                               0.87 35    0.40  30                 __________________________________________________________________________      MEK: Methyl Ethyl Ketone, THF: Tetrahydrofuran, Anone: Cyclohexanone     

EXAMPLE V-18 TO V-38

The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the antioxidant used in the photoconductive layer coating liquid in Example V-1 was replaced by the respective antioxidants as shown in TABLE 58.

Thus, electrophotographic photoconductors No. V-18 to No. V-38 according to the present invention were obtained.

                  TABLE 58                                                         ______________________________________                                         Example No.                                                                             Antioxidant                                                           ______________________________________                                         Ex. V-18 3,5-di-t-butyl-4-hydroxytoluene (made by                                       Tokyo Kasei Kogyo Co., Ltd.)                                          Ex. V-19 Trademark "SUMILIZER MDP-S", made by                                           Sumitomo Chemical Co., Ltd.                                           Ex. V-20 Trademark "SUMILIZER TPM", made by                                             Sumitomo Chemical Co., Ltd.                                           Ex. V-21 Trademark "SANOL LS-2626", made by Sankyo                                      Company, Limited                                                      Ex. V-22 Trademark "MARK PEP-24", made by Asahi                                         Denka Kogyo K.K.                                                      Ex. V-23 Trademark "IRGANOX-1330", made by CIBA-                                        GEIGY, Ltd.                                                           Ex. V-24 Compound No. (I)-13                                                   Ex. V-25 Compound No. (II)-2                                                   Ex. V-26 Compound No. (III)-1                                                  Ex. V-27 Compound No. (III)-20                                                 Ex. V-28 Compound No. (V)-49                                                   Ex. V-29 Compound No. (V)-72                                                   Ex. V-30 Compound No. (VI)-6                                                   Ex. V-31 Compound No. (VII)-18                                                 Ex. V-32 Compound No. (VIII)-23                                                Ex. V-33 Compound No. (IX)-1                                                   Ex. V-34 Compound No. (X)-6                                                    Ex. V-35 Compound No. (X)-21                                                   Ex. V-36 Compound No. (XI)-2                                                   Ex. V-37 Compound No. (XI)-20                                                  Ex. V-38 Compound No. (XII)-4                                                  ______________________________________                                    

EXAMPLE V-39

The procedure for preparation of the electrophotographic photoconductor No. V-25 in Example V-25 was repeated except that the amount of the antioxidant (Compound No. II-2 in TABLE 37) used in the photoconductive layer coating liquid in Example V-25 was changed from 5 parts by weight to 0.05 parts by weight.

Thus, an electrophotographic photoconductor No. V-39 according to the present invention was obtained.

EXAMPLE V-40

The procedure for preparation of the electrophotographic photoconductor No. V-25 in Example V-25 was repeated except that the amount of the antioxidant (Compound No. II-2 in TABLE 37) used in the photoconductive layer coating liquid in Example V-25 was changed from 5 parts by weight to 0.1 parts by weight.

Thus, an electrophotographic photoconductor No. V-40 according to the present invention was obtained.

EXAMPLE V-41

The procedure for preparation of the electrophotographic photoconductor No. V-25 in Example V-25 was repeated except that the amount of the antioxidant (Compound No. II-2 in TABLE 37) used in the photoconductive layer coating liquid in Example V-25 was changed from 5 parts by weight to 20 parts by weight.

Thus, an electrophotographic photoconductor No. V-41 according to the present invention was obtained.

EXAMPLE V-42

The procedure for preparation of the electrophotographic photoconductor No. V-25 in Example V-25 was repeated except that the amount of the antioxidant (Compound No. II-2 in TABLE 37) used in the photoconductive layer coating liquid in Example V-25 was changed from 5 parts by weight to 30 parts by weight.

Thus, an electrophotographic photoconductor No. V-42 according to the present invention was obtained.

The dynamic electrostatic properties of each of the electrophotographic photoconductors No. V-1 and Nos. V-18 to V-42 according to the present invention were measured by using a commercially available test apparatus (Trademark "EPA-8100", made by Kawaguchi Electro Works Co., Ltd.) under the circumstances of 25° C. and 50% RH.

More specifically, each photoconductor was charged positively in the dark under application of +6 kV for 10 seconds. Then, each photoconductor was allowed to stand in the dark for 20 seconds without applying any charge thereto. After that, the photoconductor was illuminated by white light of a halogen lamp in such a manner that the illuminance on the illuminated surface of the photoconductor was 10 lux.

The charging potential was expressed by a saturated surface potential Vm (V), which was obtained in the charging time of ten seconds; the photosensitivity was expressed by an exposure E_(1/2) (lux·sec) required to reduce the surface potential obtained just before the exposure to 1/2 the surface potential; and the residual potential was expressed by a surface potential V₃₀ (V) obtained 30 seconds after the exposure.

In addition, to evaluate the stability of the electrostatic properties of the photoconductor, the saturated surface potential Vm' (V), the exposure E_(1/2') (lux·sec), and the surface potential V_(30') were measured in the same manner as described above after fatigue of making of 5,000 copies.

The results are shown in TABLE 59.

                  TABLE 59                                                         ______________________________________                                         Before fatigue      After fatigue                                              Vm         E.sub.1/2 V30'   Vm'   E.sub.1/2 '                                                                            V30'                                 (V)        (lux · sec)                                                                     (V)    (V)   (lux · sec)                                                                   (V)                                  ______________________________________                                         Ex. V-1                                                                               980     1.00      45   820   1.35    85                                 Ex. V-18                                                                              720     0.82      35   550   0.98    40                                 Ex. V-19                                                                              730     0.85      40   580   0.93    50                                 Ex. V-20                                                                              725     0.80      45   585   0.92    50                                 Ex. V-21                                                                              710     0.82      45   560   0.95    55                                 Ex. V-22                                                                              700     0.81      35   545   0.97    40                                 Ex. V-23                                                                              705     0.86      45   550   0.98    50                                 Ex. V-24                                                                              950     0.81      40   850   0.83    55                                 Ex. V-25                                                                              1050    0.82      40   970   0.84    60                                 Ex. V-26                                                                              1010    0.81      40   950   0.84    55                                 Ex. V-27                                                                              990     0.85      40   900   0.93    55                                 Ex. V-28                                                                              920     0.83      45   830   0.87    65                                 Ex. V-29                                                                              950     0.84      40   800   0.90    60                                 Ex. V-30                                                                              940     0.82      40   830   0.87    55                                 Ex. V-31                                                                              945     0.84      40   825   0.90    60                                 Ex. V-32                                                                              960     0.83      40   850   0.90    55                                 Ex. V-33                                                                              955     0.82      40   840   0.88    55                                 Ex. V-34                                                                              940     0.85      40   810   0.90    55                                 Ex. V-35                                                                              935     0.86      40   800   0.94    55                                 Ex. V-36                                                                              955     0.88      45   815   0.97    65                                 Ex. V-37                                                                              940     0.90      45   795   0.98    70                                 Ex. V-38                                                                              1000    0.84      40   830   0.88    60                                 Ex. V-39                                                                              920     0.80      35   590   0.92    40                                 Ex. V-40                                                                              990     0.81      40   830   0.83    50                                 Ex. V-41                                                                              1180    0.90      60   1120  1.25    80                                 Ex. V-42                                                                              1250    1.02      85   1180  1.55    120                                ______________________________________                                    

As is apparent from the results shown in TABLE 59, the charging characteristics of the photoconductor are remarkably improved when the single-layered photoconductive layer comprises an antioxidant. In particular, the charging characteristics are excellent and the photosensitivity and residual potential are advantageous in Examples V-24 to V-38 in which antioxidants of formulas (I) to (XII) are employed, and in Examples V-40 and V-41 in which the amount of the antioxidant contained in the photoconductive layer is preferable.

As previously explained, the electrophotographic photoconductors according to the present invention exhibit high photosensitivity in a broad wave range from the visible region extending to the near infrared region, and excellent charging stability when the single-layered photoconductive layer comprises a simultaneously pulverized mixture comprising the disazo pigment of formula (1) and the trisazo pigment of formula (2), the charge transporting material, the binder resin and the antioxidant. In this case, the decrease of image density and the toner deposition on the background can be prevented.

Japanese Patent Application 5-280543 filed on Oct. 14, 1993; Japanese Patent Application 5-354296 filed on Dec. 30, 1993; Japanese Patent Application 5-354295 filed on Dec. 30, 1993; Japanese Patent Application 5-341779 filed on Dec. 11, 1993; and Japanese Patent Application 6-193563 filed on Jul. 26, 1994 are hereby incorporated by reference. 

What is claimed is:
 1. An electrophotographic photoconductor comprising an electroconductive support and a single-layered photoconductive layer formed thereon, comprising:(a) a charge transporting material, (b) a binder resin, and (c) a simultaneously pulverized mixture comprising at least one disazo pigment of formula (1) and at least one trisazo pigment of formula (2), which is obtained by simultaneously pulverizing said disazo pigment and said trisazo pigment: ##STR2034## wherein R¹ and R² each is hydrogen, a halogen atom, trifluoromethyl group, nitro group or cyano group; R³ is hydrogen, chlorine, fluorine, iodine, bromine, nitro group or cyano group; and Ar¹, Ar² and Ar³ each is a coupler radical, which may be the same or different, and is selected from the group consisting of coupler radicals of formulas (3) to (10): ##STR2035## wherein X¹ is --OH, --N(R⁴)(R⁵), or --NHSO₂ R⁶, in which R⁴ and R⁵ each is hydrogen, an acyl group or an alkyl group which may have a substituent, and R⁶ is an aryl group which may have a substituent; Y¹ is hydrogen, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group, a carboxyl group, a sulfone group, a benzimidazolyl group, a sulfamoyl group which may have a substituent, or --CON(R⁷)(Y²), in which R⁷ is hydrogen, an alkyl group which may have a substituent, or a phenyl group which may have a substituent, and Y² is a cyclic hydrocarbon group which may have a substituent, a heterocyclic group which may have a substituent, or --N═C(R⁸)(R⁹), in which R⁸ is a cyclic hydrocarbon group which may have a substituent, a heterocyclic group which may have a substituent, or a styryl group which may have a substituent, R⁹ is hydrogen, an alkyl group which may have a substituent, or a phenyl group which may have a substituent, and R⁸ and R⁹ may form a ring in combination with a carbon atom to which R⁸ and R⁹ are bonded; and Z is a cyclic hydrocarbon group which may have a substituent, or a heterocyclic group which may have a substituent; ##STR2036## wherein n is an integer of 1 to 4; R¹⁰ is hydrogen, an alkyl group which may have a substituent, or an aryl group which may have a substituent; R¹¹ is hydrogen, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an alkylsulfonyl group which may have a substituent, an alkylmercapto group which may have a substituent, a halogen atom, an aryl group which may have a substituent, an acyl group which may have a substituent, cyano group, nitro group, or an amino group which may have a substituent, and when n is 2, 3 or 4, R¹¹ may be the same or different; and Y¹ is the same as defined in formula (3); ##STR2037## ##STR2038## wherein R¹² in formulas (5) and (6) is a hydrocarbon group which may have a substituent; ##STR2039## wherein R¹³ in formulas (7) and (8) is an alkyl group, a carbamoyl group, a carboxyl group or an ester group thereof; and Ar⁴ is an aromatic hydrocarbon group which may have a substituent; ##STR2040## wherein X² in formulas (9) and (10) is a bivalent aromatic hydrocarbon group or a bivalent heterocyclic group.
 2. The electrophotographic photoconductor as claimed in claim 1, wherein said trisazo pigment is a compound of formula (11): ##STR2041## wherein R³¹ to R³⁹ each is hydrogen, --CH₃, --C₂ H₅, --C₃ H₇, chlorine, fluorine, iodine, bromine, CH₃ --, C₂ H₅ O--, C₃ H₇ O--, --NO₂, --CN, --CF₃ or --OH.
 3. The electrophotographic photoconductor as claimed in claim 1, wherein said disazo pigment is selected from the group consisting of a compound of formula (12) and a compound of formula (13): ##STR2042##
 4. The electrophotographic photoconductor as claimed in claim 1, wherein the amount of said simultaneously pulverized mixture of said disazo pigment and said trisazo pigment is in a range of 0.01 to 10 parts by weight to 10 parts by weight of said binder resin.
 5. The electrophotographic photoconductor as claimed in claim 1, wherein said charge transporting material is an organic positive hole transporting material and is contained in said single-layered photoconductive layer in an amount of 1 to 15 parts by weight to 10 parts by weight of said binder resin.
 6. The electrophotographic photoconductor as claimed in claim 1, wherein said charge transporting material has an oxidation potential of +0.5 V (vs SCE) or more.
 7. The electrophotographic photoconductor as claimed in claim 6, wherein said charge transporting material comprises at least one compound of formula (14) having an oxidation potential of +0.5 V (vs SCE) or more: ##STR2043## wherein R¹ is methyl group, ethyl group, 2-hydroxyethyl group or 2-chloroethyl group; R² is methyl group, ethyl group, benzyl group or phenyl group; and R³ is hydrogen, chlorine, bromine, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a dialkylamino group, or nitro group.
 8. The electrophotographic photoconductor as claimed in claim 6, wherein said charge transporting material comprises at least one compound of formula (15) having an oxidation potential of +0.5 V (vs SCE) or more: ##STR2044## wherein Ar is naphthalene ring, anthracene ring, styryl ring, each of which may have a substituent, pyridyl ring, furan ring, or thiophene ring; and R is an alkyl group or benzyl group.
 9. The electrophotographic photoconductor as claimed in claim 6, wherein said charge transporting material comprises at least one compound of formula (17) having an oxidation potential of +0.5 V (vs SCE) or more: ##STR2045## wherein R¹ is an alkyl group having 1 to 11 carbon atoms, a substituted or unsubstituted phenyl group, or a heterocyclic group; R² and R³ may be the same or different and each is hydrogen, an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group, a chloroalkyl group, or a substituted or unsubstituted aralkyl group, and R² and R³ may form a nitrogen-containing heterocyclic ring in combination; and R⁴ is hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group, or a halogen atom, and may be the same or different.
 10. The electrophotographic photoconductor as claimed in claim 6, wherein said charge transporting material comprises at least one compound of formula (19) having an oxidation potential of +0.5 V (vs SCE) or more: ##STR2046## wherein R is hydrogen or a halogen atom; Ar is phenyl group, naphthyl group, anthryl group or carbazolyl group, each of which may have a substituent.
 11. The electrophotographic photoconductor as claimed in claim 6, wherein said charge transporting material comprises at least one compound of formula (22) having an oxidation potential of +0.5 V (vs SCE) or more: ##STR2047## wherein R¹ is a lower alkyl group, a substituted or unsubstituted phenyl group, or benzyl group; R² and R³ each is hydrogen, a lower alkyl group, a lower alkoxyl group, a halogen atom, nitro group, or an amino group which may have as a substituent a lower alkyl group or benzyl group; and n is an integer of 1 or
 2. 12. The electrophotographic photoconductor as claimed in claim 6, wherein said charge transporting material comprises at least one compound of formula (23) having an oxidation potential of +0.5 V (vs SCE) or more: ##STR2048## wherein R¹ is hydrogen, an alkyl group, an alkoxyl group or a halogen atom; R² and R³ each is an alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group; R⁴ is hydrogen, a lower alkyl group, or a substituted or unsubstituted phenyl group; and Ar is a substituted or unsubstituted phenyl group or naphthyl group.
 13. The electrophotographic photoconductor as claimed in claim 6, wherein said charge transporting material comprises at least one compound of formula (24) having an oxidation potential of +0.5 V (vs SCE) or more: ##STR2049## wherein n is an integer of 0 or 1; R¹ is hydrogen, an alkyl group or a substituted or unsubstituted phenyl group; Ar¹ is a substituted or unsubstituted aryl group; R⁵ is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; and A is ##STR2050## 9-anthryl group or a substituted or unsubstituted N-alkylcarbazolyl group, in which R² is hydrogen, an alkyl group, an alkoxyl group, a halogen atom, or ##STR2051## in which R³ and R⁴ each is an alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group, and R³ and R⁴ may be the same or different and may form a ring in combination; m is an integer of 0 to 3; and when m is 2 or more, R² may be the same or different; and when n is 0, A and R¹ may form a ring in combination.
 14. The electrophotographic photoconductor as claimed in claim 6, wherein said charge transporting material comprises at least one compound of formula (28) having an oxidation potential of +0.5 V (vs SCE) or more: ##STR2052## wherein R¹ is a lower alkyl group, a lower alkoxyl group, or a halogen atom; n is an integer of 0 to 4; and R² and R³ may be the same or different, and each is hydrogen, a lower alkyl group, a lower alkoxyl group, or a halogen atom.
 15. The electrophotographic photoconductor as claimed in claim 6, wherein said charge transporting material comprises at least one compound of formula (29) having an oxidation potential of +0.5 V (vs SCE) or more: ##STR2053## wherein R¹, R³ and R⁴ each is hydrogen, an amino group, a thioalkoxyl group, an aryloxy group, methylenedioxy group, a substituted or unsubstituted alkyl group, a halogen atom, or a substituted or unsubstituted aryl group; R² is hydrogen, an alkoxyl group, a substituted or unsubstituted alkyl group, or a halogen atom, provided that not all of R¹, R², R³, and R⁴ are hydrogen at the same time; k, l, m and n each is an integer of 1 to 4, and when each of k, l, m and n is 2, 3 or 4, R¹, R², R³, and R⁴ may be the same or different.
 16. The electrophotographic photoconductor as claimed in claim 6, wherein said charge transporting material comprises at least one compound of formula (30) having an oxidation potential of +0.5 V (vs SCE) or more: ##STR2054## wherein Ar is a condensed polycyclic hydrocarbon group having 18 or less carbon atoms; R¹ and R² may be the same or different, and each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxyl group, or a substituted or unsubstituted phenyl group.
 17. The electrophotographic photoconductor as claimed in claim 6, wherein said charge transporting material comprises at least one compound of formula (31) having an oxidation potential of +0.5 V (vs SCE) or more:

    A--CH═CH--Ar--CH═CH--A                             (31)

wherein Ar is a substituted or unsubstituted aromatic hydrocarbon group; and A is ##STR2055## in which Ar' is a substituted or unsubstituted aromatic hydrocarbon group; and R¹ and R² each is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
 18. The electrophotographic photoconductor as claimed in claim 1, wherein said simultaneously pulverized mixture is prepared by simultaneously mixing and pulverizing said disazo pigment and said trisazo pigment by use of at least one dispersing solvent selected from the group consisting of a cyclic ether and a cyclic ketone.
 19. The electrophotographic photoconductor as claimed in claim 1, wherein said simultaneously pulverized mixture is prepared by simultaneously mixing and pulverizing said disazo pigment and said trisazo pigment by use of at least one dispersing solvent selected from the group consisting of tetrahydrofuran and cyclohexanone.
 20. The electrophotographic photoconductor as claimed in claim 1, wherein said charge transporting material comprises an organic positive hole transporting material and an organic acceptor compound.
 21. The electrophotographic photoconductor as claimed in claim 20, wherein the amount of said organic acceptor compound is in a range of 1 to 15 parts by weight to 10 parts by weight of said binder resin.
 22. The electrophotographic photoconductor as claimed in claim 20, wherein said organic acceptor compound is a compound of formula (1): ##STR2056## wherein R¹ is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, an alkoxycarbonyl group, an N-alkylcarbamoyl group, cyano group or nitro group; n is an integer of 1 to 3; X is ##STR2057## in which R² and R³ each is an alkyl group, and R³ may be bonded to each other.
 23. The electrophotographic photoconductor as claimed in claim 20, wherein said organic acceptor compound is a compound of formula (2): ##STR2058## wherein Ar is a substituted or unsubstituted aromatic group; and X is cyano group or an alkoxycarbonyl group.
 24. The electrophotographic photoconductor as claimed in claim 20, wherein said organic acceptor compound is a compound of formula (3):

    Ar--CH═C(COOR).sub.2                                   ( 3)

wherein Ar is a substituted or unsubstituted aromatic group; and R is an alkyl group, and R may be bonded to each other to form a ring.
 25. The electrophotographic photoconductor as claimed in claim 20, wherein said organic acceptor compound is a compound of formula (4): ##STR2059## wherein X is sulfur or selenium; Y is a substituted or unsubstituted alkyl group, an aryl group, or cyano group; R is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, cyano group, nitro group, a halogen atom, or hydrogen; and n is an integer of 1 to
 3. 26. The electrophotographic photoconductor as claimed in claim 20, wherein said organic acceptor compound is a compound of formula (5):

    Ar--CH═CHNO.sub.2                                      ( 5)

wherein Ar is a substituted or unsubstituted aromatic group.
 27. The electrophotographic photoconductor as claimed in claim 20, wherein said organic acceptor compound is a compound of formula (6): ##STR2060## wherein R¹ and R² each is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a heterocyclic aromatic group.
 28. The electrophotographic photoconductor as claimed in claim 20, wherein said organic acceptor compound is a compound of formula (7): ##STR2061## wherein R¹ is hydrogen, a halogen atom, an alkyl group, or a substituted or unsubstituted phenyl group; R² is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, a halogen atom, an alkoxycarbonyl group, an N-alkylcarbamoyl group, cyano group, or nitro group; and n is an integer of 1 to
 3. 29. The electrophotographic photoconductor as claimed in claim 20, wherein said organic acceptor compound is a compound of formula (8): ##STR2062## wherein R³ is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, a halogen atom, an alkoxycarbonyl group, an N-alkylcarbamoyl group, cyano group, or nitro group; and n is an integer of 1 to
 3. 30. The electrophotographic photoconductor as claimed in claim 20, wherein said organic acceptor compound is a compound of formula (9): ##STR2063## wherein R¹ and R² each is a substituted or unsubstituted phenyl group, a substituted or unsubstituted polycyclic aromatic group, or a substituted or unsubstituted heterocyclic group.
 31. The electrophotographic photoconductor as claimed in claim 20, wherein said organic acceptor compound is a compound of formula (10): ##STR2064## wherein R¹ and R² each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, an N-alkylcarbamoyl group, an alkylcarbonyl group, an arylcarbonyl group, cyano group, nitro group, an alkoxyl group, an aryloxy group, an amino group, or a vinyl group of ##STR2065## in which X is hydrogen or an alkyl group, and at least one of Y or Z is a substituted or unsubstituted phenyl group and the other is hydrogen; and n and m each is an integer of 1 to
 3. 32. The electrophotographic photoconductor as claimed in claim 20, wherein said organic acceptor compound is a compound of formula (11): ##STR2066## wherein R³ and R⁴ each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, an N-alkylcarbamoyl group, an alkylcarbonyl group, an arylcarbonyl group, cyano group, nitro group, an alkoxyl group, an aryloxy group, an amino group, or a vinyl group of ##STR2067## in which X is hydrogen or an alkyl group, and at least one of Y or Z is a substituted or unsubstituted phenyl group and the other is hydrogen; and n and m each is an integer of 1 to
 3. 33. The electrophotographic photoconductor as claimed in claim 20, wherein said organic acceptor compound is a compound of formula (12): ##STR2068## wherein R⁵ and R⁶ each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, an N-alkylcarbamoyl group, an alkylcarbonyl group, an arylcarbonyl group, cyano group, nitro group, an alkoxyl group, an aryloxy group, an amino group, or a vinyl group of ##STR2069## in which X is hydrogen or an alkyl group, and at least one of Y or Z is a substituted or unsubstituted phenyl group and the other is hydrogen; and n and m each is an integer of 1 to
 3. 34. The electrophotographic photoconductor as claimed in claim 20, wherein said organic acceptor compound is a compound of formula (13): ##STR2070## wherein R⁷ and R⁸ each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, an N-alkylcarbamoyl group, an alkylcarbonyl group, an arylcarbonyl group, cyano group, nitro group, an alkoxyl group, an aryloxy group, an amino group, or a vinyl group of ##STR2071## in which X is hydrogen or an alkyl group, and at least one of Y or Z is a substituted or unsubstituted phenyl group and the other is hydrogen; and n and m each is an integer of 1 to
 3. 35. The electrophotographic photoconductor as claimed in claim 20, wherein said organic acceptor compound is a compound of formula (14): ##STR2072## wherein X is O or N--R, in which R is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.
 36. The electrophotographic photoconductor as claimed in claim 20, wherein said organic acceptor compound is a compound of formula (A): ##STR2073## wherein R¹, R², and R³ each is hydrogen, a substituted or unsubstituted alkyl group, an alkoxyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted sulfonamide group, a substituted or unsubstituted carbamoyl group, a halogen atom, cyano group, or nitro group, and R¹ may form a ring in combination with other atoms; k, l and m each is an integer of 1 to 4; and X is oxygen, sulfur or selenium.
 37. The electrophotographic photoconductor as claimed in claim 20, wherein said organic acceptor compound is a compound of formula (B): ##STR2074## wherein R¹, R², R³ and R⁴ may be the same or different, and each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, cyano group, or nitro group; and X is ##STR2075## in which R⁵ and R⁶ may be the same or different and each is hydrogen, a halogen atom, cyano group, a substituted or unsubstituted aromatic group, or --COOR⁷ in which R⁷ is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic group; orN--R⁸ in which R⁸ is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, or cyano group.
 38. The electrophotographic photoconductor as claimed in claim 20, wherein said organic acceptor compound is a compound of formula (C): ##STR2076## wherein R¹ may be the same or different, and is a halogen atom, nitro group, or a substituted or unsubstituted alkyl group; X is ═O, N--R²,in which R² is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group, or ##STR2077## in which R³ and R⁴ may be the same or different and each is hydrogen, cyano group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted phenoxycarbonyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group; and p is an integer of 0 to 4, provided that when X is oxygen, p is an integer of 1 to
 4. 39. The electrophotographic photoconductor as claimed in claim 20, wherein said organic acceptor compound has a reduction potential in a range of -0.2 to -1.2 V (vs SCE).
 40. The electrophotographic photoconductor as claimed in claim 1, wherein said photoconductive layer further comprises an antioxidant.
 41. The electrophotographic photoconductor as claimed in claim 40, wherein said antioxidant is contained in said photoconductive layer in an amount of 0.01 to 2 parts by weight to 10 parts by weight of said binder resin.
 42. The electrophotographic photoconductor as claimed in claim 40, said antioxidant comprises a compound of formula (I): ##STR2078## wherein R¹, R², R³ and R⁴ each is hydrogen, a halogen atom, hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted amino group, imino group, a heterocyclic group, a sulfoxide group, a sulfonyl group, an acyl group, or an azo group.
 43. The electrophotographic photoconductor as claimed in claim 40, said antioxidant comprises a compound of formula (II): ##STR2079## wherein R¹, R², R³ and R⁴ each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, an alkylthio group, an arylthio group, an alkylamino group, an arylamino group, an acyl group, an alkylacylamino group, an arylacylamino group, an alkylcarbamoyl group, an arylcarbamoyl group, an alkylsulfonamide group, an arylsulfonamide group, an alkylsulfamoyl group, an arylsulfamoyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, an alkylacyloxy group, an arylacyloxy group, a silyl group, or a heterocyclic group, provided that at least one of R¹, R², R³ or R⁴ is a group having 4 or more carbon atoms.
 44. The electrophotographic photoconductor as claimed in claim 40, said antioxidant comprises a compound of formula (III): ##STR2080## wherein R¹ to R⁸ each is hydrogen, a hydroxyl group, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted phosphonyl group, or a substituted or unsubstituted carbamoyl group.
 45. The electrophotographic photoconductor as claimed in claim 40, said antioxidant comprises a compound of formula (IV): ##STR2081## wherein R¹ to R⁷ each is hydrogen, a hydroxyl group, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted phosphonyl group, or a substituted or unsubstituted carbamoyl group.
 46. The electrophotographic photoconductor as claimed in claim 40, said antioxidant comprises a compound of formula (V): ##STR2082## wherein R¹ to R⁷ each is hydrogen, a hydroxyl group, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted phosphonyl group, or a substituted or unsubstituted carbamoyl group.
 47. The electrophotographic photoconductor as claimed in claim 40, said antioxidant comprises a compound of formula (VI): ##STR2083## wherein R¹ to R⁶ each is hydrogen, a hydroxyl group, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted phosphonyl group, or a substituted or unsubstituted carbamoyl group.
 48. The electrophotographic photoconductor as claimed in claim 40, said antioxidant comprises a compound of formula (VII): ##STR2084## wherein R¹ to R⁸ each is hydrogen, a hydroxyl group, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted phosphonyl group, or a substituted or unsubstituted carbamoyl group.
 49. The electrophotographic photoconductor as claimed in claim 40, said antioxidant comprises at least one of a compound of formula (VIII) or a compound of formula (IX): ##STR2085## wherein R¹ to R¹⁰ and R¹¹ to R¹⁸ each is hydrogen, a halogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted amino group, an imino group, a heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a sulfoxide group, a sulfonyl group, an acyl group, or an azo group.
 50. The electrophotographic photoconductor as claimed in claim 40, said antioxidant comprises at least one of a compound of formula (X) or a compound of formula (XI): ##STR2086## wherein R¹ to R⁸ and R⁹ to R¹⁸ each is hydrogen, a halogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted amino group, an imino group, a heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a sulfoxide group, a sulfonyl group, an acyl group, or an azo group.
 51. The electrophotographic photoconductor as claimed in claim 40, said antioxidant comprises a compound of formula (XII): ##STR2087## wherein R¹ to R⁵ each is hydrogen, a halogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted amino group, an imino group, a heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a sulfoxide group, a sulfonyl group, an acyl group, or an azo group.
 52. The electrophotographic photoconductor as claimed in claim 1, wherein said at least one disazo pigment of the formula (1) and said at least one trisazo pigment of the formula (2) are used in a ratio of: ##EQU1##
 53. The electrophotographic photoconductor as claimed in claim 52, wherein said ratio is: ##EQU2##
 54. The electrophotographic photoconductor as claimed in claim 1, wherein said single-layered photoconductive layer has a thickness of from 5 to 100 μm.
 55. The electrophotographic photoconductor as claimed in claim 54, wherein said single-layered photosensitive layer has a thickness of from 10 to 50 μm. 